Advice on Rogue Multiclass Character Build for OotA

[GTNE90]

Hey All,
I would like some advice on a character build.
Background:
My gaming group’s DM wants to run Out of the Abyss (OotA) as our next campaign/storyline. Per the back cover, OotA will be focused in the Underdark, has demons as an adversary, and cover levels 1-15. I can expect a total of 15 levels max for the character.

I was thinking of making a Rogue character with a Perception & Stealth focus, maybe leading to the Scout Archetype, but am open to others (Assassin and Swashbuckler being prime). I was considering dipping into Ranger for 3-5 levels for the Gloom Strider Archetype features and Extra Attack options, and maybe also dipping into Monk for 3-6 levels for the Kensei Archetype features. A dip into Fighter for 2 levels for a second fighting style and Action Surge are also possible.

The draft level 1 build and some questions are all below.

Thanks in advance for your thoughts, advice, and feedback.
-Dan

Draft Level 1 Build:
Wood Elf Rogue (Level 1) Outlander 5’4” 120 lbs
S10 (+0) D16 (+3) C13 (+1) I12 (+1) W16 (+3) C8 (-1)
AC 14 HP 9 Speed 35ft PP 17 PI 13
Proficiency - Armor: Light,
Proficiency - Weapons: Simple, Rapiers, Hand crossbow, Shortswords, Longsword, shortbow, longbow
Proficiency – Thieves Tools
Proficiency – Skills: Acrobatics+5, Athletics +2, Insight +5, Investigation +3, Perception +7, Stealth+7, Survival +5
Proficiency – Languages: Elvish, Common, Undercommon
Equipment: Leather armor, 2 daggers, thieves tools, shortswords, explorers pack, shortbow and 20 arrows, staff, hunting trap, owlbear claw, traveler’s clothes, belt pouch, 10gp
Personality: Driven by wanderlust (O1), Protect friends (O2)
Ideal: Honor (O3)
Bond: Importance of my order (O1)
Flaw:too enamored of intoxicants (O1)
Feature: Wanderer
Traits - Elf: Darkvision, Keen Senses, Fey Ancestry, Trance, Fleet of Foot, Mask of Wild
Traits – Rogue:
1st: Expertise, Sneak Attack (+1d6), Thieves; Cant

Questions:
1) What do you think about the above draft build?
2) What do you think about a Rogue(Scout), compared to Rogue(Assassin) or Rogue(Swashbuckler?
3) Should I plan to go to Rogue Level 3 (for the Archetype features) or Level 4 (for the Feat/ASI) before changing class?
4) If 4th level Rogue, what is your opinion on taking the ASI on Dexterity or the Sharpshooter Feat?
5) What do you think about the Ranger(Gloom Stalker) compared to the Ranger(Hunter) or Ranger(Monster Slayer) or other Ranger archetype?
6) I was thinking the Archery fighting style, or does the two weapon fighting style seem better, or does it depend on the party mix (tank or not)?
7) Should I plan to go to Ranger Level 3 (for the Archetype features), Level 4 for the Feat/ASI), or Level 5 for the 2nd Attack before changing class?
8) If 4th or higher Ranger, what is your opinion of taking the ASI on Dexterity, Sharpshooter Feat (if not chosen previously), or the Alert Feat?
9) What is your opinion on the second dip/dive into Monk levels, versus more Rogue or Ranger, or going Fighter?
10) What do you think about Monk(Kensei), compared to Monk(Way of Shadows) or Monk (Open Hand) or other Monk archetype/tradition?
11) If I add Monk, should I go to Level 3 (for the Archetype features), level 4 (for the Feat/ASI), Level 5 (for extra attack if didn’t already in ranger, and other features), or Level 6th (for the Archetype features)?
12) If 4th level or higher Monk, what is your opinion of taking the ASI on Dexterity (if not already maxed), the ASI on Wisdom or another ability, the Sharpshooter Feat (if not chosen previously), the Alert Feat (if not already taken), or another Feat?
13) If haven’t used up the 15 level, where do you think the remain ones should be spent? Rogue for better sneak attack and features (uncanny dodge, expertise, evasion, etc.)? Ranger for extra spells and features (favored enemy, iron mind, etc)? Monk for features? A dip into fighter for a second fighting style and features such as Action Surge?
14) Any other advice or thoughts?

[CTurbo]

Hey All,
I would like some advice on a character build.
Background:
My gaming group’s DM wants to run Out of the Abyss (OotA) as our next campaign/storyline. Per the back cover, OotA will be focused in the Underdark, has demons as an adversary, and cover levels 1-15. I can expect a total of 15 levels max for the character.

I was thinking of making a Rogue character with a Perception & Stealth focus, maybe leading to the Scout Archetype, but am open to others (Assassin and Swashbuckler being prime). I was considering dipping into Ranger for 3-5 levels for the Gloom Strider Archetype features and Extra Attack options, and maybe also dipping into Monk for 3-6 levels for the Kensei Archetype features. A dip into Fighter for 2 levels for a second fighting style and Action Surge are also possible.

The draft level 1 build and some questions are all below.

Thanks in advance for your thoughts, advice, and feedback.
-Dan

Draft Level 1 Build:
Wood Elf Rogue (Level 1) Outlander 5’4” 120 lbs
S10 (+0) D16 (+3) C13 (+1) I12 (+1) W16 (+3) C8 (-1)
AC 14 HP 9 Speed 35ft PP 17 PI 13
Proficiency - Armor: Light,
Proficiency - Weapons: Simple, Rapiers, Hand crossbow, Shortswords, Longsword, shortbow, longbow
Proficiency – Thieves Tools
Proficiency – Skills: Acrobatics+5, Athletics +2, Insight +5, Investigation +3, Perception +7, Stealth+7, Survival +5
Proficiency – Languages: Elvish, Common, Undercommon
Equipment: Leather armor, 2 daggers, thieves tools, shortswords, explorers pack, shortbow and 20 arrows, staff, hunting trap, owlbear claw, traveler’s clothes, belt pouch, 10gp
Personality: Driven by wanderlust (O1), Protect friends (O2)
Ideal: Honor (O3)
Bond: Importance of my order (O1)
Flaw:too enamored of intoxicants (O1)
Feature: Wanderer
Traits - Elf: Darkvision, Keen Senses, Fey Ancestry, Trance, Fleet of Foot, Mask of Wild
Traits – Rogue:
1st: Expertise, Sneak Attack (+1d6), Thieves; Cant

Questions:
1) What do you think about the above draft build?
2) What do you think about a Rogue(Scout), compared to Rogue(Assassin) or Rogue(Swashbuckler?
3) Should I plan to go to Rogue Level 3 (for the Archetype features) or Level 4 (for the Feat/ASI) before changing class?
4) If 4th level Rogue, what is your opinion on taking the ASI on Dexterity or the Sharpshooter Feat?
5) What do you think about the Ranger(Gloom Stalker) compared to the Ranger(Hunter) or Ranger(Monster Slayer) or other Ranger archetype?
6) I was thinking the Archery fighting style, or does the two weapon fighting style seem better, or does it depend on the party mix (tank or not)?
7) Should I plan to go to Ranger Level 3 (for the Archetype features), Level 4 for the Feat/ASI), or Level 5 for the 2nd Attack before changing class?
8) If 4th or higher Ranger, what is your opinion of taking the ASI on Dexterity, Sharpshooter Feat (if not chosen previously), or the Alert Feat?
9) What is your opinion on the second dip/dive into Monk levels, versus more Rogue or Ranger, or going Fighter?
10) What do you think about Monk(Kensei), compared to Monk(Way of Shadows) or Monk (Open Hand) or other Monk archetype/tradition?
11) If I add Monk, should I go to Level 3 (for the Archetype features), level 4 (for the Feat/ASI), Level 5 (for extra attack if didn’t already in ranger, and other features), or Level 6th (for the Archetype features)?
12) If 4th level or higher Monk, what is your opinion of taking the ASI on Dexterity (if not already maxed), the ASI on Wisdom or another ability, the Sharpshooter Feat (if not chosen previously), the Alert Feat (if not already taken), or another Feat?
13) If haven’t used up the 15 level, where do you think the remain ones should be spent? Rogue for better sneak attack and features (uncanny dodge, expertise, evasion, etc.)? Ranger for extra spells and features (favored enemy, iron mind, etc)? Monk for features? A dip into fighter for a second fighting style and features such as Action Surge?
14) Any other advice or thoughts?



Rogue/Ranger is extremely strong. Gloom Stalker is perfect for you. I'd take Gloom Stalker 5 probably.

1) Pretty good draft. I would not settle for a Con lower than 14. Do you need a Wis that high?
2) I like Scout for Archers. Assassin is best for somebody who wants to dip Rogue for a few levels as it's incredibly front loaded much like Gloom Stalker. Assassin and Gloom Stalker mesh perfectly though. Swashbuckler is great, but you'd want a lot more Cha. I say go Scout if you plan to more mostly ranged, Swashbuckler if you plan to be mostly melee, and Assassin for an even mix.
3) I would either start Rogue 1, then go Ranger 5, then back to Rogue, or start Rogue 5 and then take Ranger 5.
4) I would 100% bump Dex to 18 ASAP.
5) Gloom Stalker is extremely powerful for small dip. You get extra far darkvision and a super powered first turn. Hunter is really good for either Horde Breaker or Colossus Slayer. The UA Revised Ranger is particularly powerful for small dips. Check with your DM to see if you can use it. The Monster Hunter doesn't really interest me.
6) Fighting Style is all up to you. Archery is great if that's how you want to play. TWF is great at low levels, but doesn't scale as well as Dueling or GWF. I'd probably only take TWF is you choose Swashbuckler and don't plan on taking more than 3 Ranger levels.
7) I'd take Ranger 5 and all in a row.
8) After Dex to 18, take Sharpshooter if you want to be ranged. Alert would be a great pick if Assassin/Gloom Stalker. Dex 20 is always great. Mobile is strong on a character like this. Magic Initiate for Find Familiar and Booming Blade would be good. Booming Blade is even better if you decide to only go Ranger 3.
9) Don't think I would take any Monk levels. Monks don't mutliclass very well as you'll never have much ki. Shadow Monk/Assassin/Gloom Stalker does have some appeal though. I'd go Ranger 3, Assassin 5, and then Monk from there if I were to attempt that.
10) As mentioned above, Shadow Monk would be strong. Open Hand is alright. I like Long Death the most though.
11) and 12) If you do decide to go Monk, You want to Max Dex AND Wis probably. This build does not really NEED many feats to be successful.
13) If you want to dip Fighter, do it late. 2 levels is enough. Taking a 3rd level in Fighter would be fine too. Either Champion or Battle Master would be great.
14) Gloom Stalker 5, Assassin 7, Champion 3 would have an outrageous first round. The Gloom Stalker's extra attack stacks with Action Surge so you'd get 6 attacks on the first round with Action Surge and they would all have advantage and possibly all be crits.

I made a Hunter/Assassin/Champion Archer once and he was awesome but it takes forever for all of that to come online or course.


Getting Dex 20 would be my top priority except for maybe Sharpshooter if you want to be ranged. Sharpshooter is not always the best for Rogues though since you're hindering your chances to land Sneak Attack.

Mobile is a must for Scout.
Alert is a must for Assassin.
MOAR Wis is a must for Monk.
MOAR Cha is a must for Swashbucklers.
Scout and Swashbuckler mesh well together.
Booming Blade is a must if never gaining a second attack.

[GTNE90]

First, thank you for the feedback. Now to the specifics … and a few more questions:
1) Thank you, I appreciate the critique. The High Wisdom build is for Perception and scouting, plus later Gloom Strider Survival boost and the far-off Monk dip. Thought is sensing danger first and running away (especially if out scouting alone) to avoid the hit is better than soaking the damage of a hit. That is my untried theory anyway. Thoughts?
2) We haven’t had a Session 0 yet, so I don’t know what the rest of the party will bring to the table. My concept leans Scout. But if the rest of the party doesn’t include a tank, I may go Assassin. I’m thinking Swashbuckler needs a different concept. May be a build starting with a Drow …
3) Rogue all the way to 5, rather than just 4 for the ASI? Is the Uncanny Dodge Feature or the 3d6 Sneak attack the driver? I was sort of prioritizing level multiples of 4 for Feat/ASI.
4) Prioritize Dex ASI bumps, check.
5) I am convinced to go Gloom Stalker for this build
6) The Archery Fighting Style will be the plan if I stick with the Scout path. If I go with the Assassin path, I wasn’t sure what Fighting Style to go with. GWF doesn’t work with Finesse weapons for Sneak Attack, so I thought it was between Dueling and TWF. Dueling’s +2 damage plus a shield versus TWF’s chance at additional damage (1d6+4 with the shortsword and Dex 18). The longer-term plan of going Monk, which doesn’t allow for a shield, lead me to think TWF. But what is the scaling issue you are talking about?
7) Ranger Levels 1 to 5 , check.
8) So if Scout & Archery, then Sharpshooter before Dex 20; if Assassin, then Alert before Dex 20; and if Swashbuckler, then Mobility before Dex 20. Plus remember to pick up Blooming Blade, check
9) The Monk-Kensei is what struck me. For the Scout & Archery build, 3rd level Kensei’s Shot adds 1d4 damage to arrow shots (no Ki cost), and 6th level Deft Strike adds 1d6 (for a cost of 1 Ki) and counting attacks as if magical (no Ki cost). For the Assassin build, the 3rd level Agile Parry for +2 AC seemed good. The Way of Shadow powers seem neat, but you are right about the Ki cost.
10) Will have to look into Long Death, is that in SCAG?
11) New options to consider …
12) As per 8, but could replace Feat with 18 Wis.
13) A late dip in fighter is what I was thinking. Action surge at 2nd level was the prime idea. Although if I can work it, there is some nice synergy with some of the Battle Master’s Combat Superiority Maneuvers (e.g., Evasive Footwork Plus Skirmisher and Dread Ambusher, etc.)
14) How are you getting 6 attacks for the Assassin 7-Gloom Stalker 5-Champion 3? I can see 2 from Extra Attack and x2 for Action Surge, and plus 1 from Dread Ambusher for 5, but not 6. Unless Action Surge doubles the Dread Ambusher one additional weapon attack or you are including the TWF bonus action attacks or Monk unarmed attacks for 6? Or are you looking at the Am I missing something?

New questions
For the Scout-Archer build (which I will start calling “Sniper” build), I think Scout 4-Gloom Strider 5 is the base. The questions become 15) How to use the last 6 levels (more Scout, more Gloom Strider, Kensei dip, etc.)? and 16) what order to build (Rogue 1, Ranger 1-5, Rogue/Scout 2-?; Scout 1-4, Gloom Strider 1-5, +?; )?

For the Assassin build (which I will start calling “First-Strike” build) I think Assassin 5-Gloom Strider 5 is the base. The questions are then 17) How to use the last 5 levels (more Assassint, more Gloom Strider, add Fighter, etc.)? and 16) what order to build (Rogue 1, Ranger 1-5, Rogue/Assassin 2-?; Assassin 1-5, Gloom Strider 1-5, +?; )?

[CTurbo]

First, thank you for the feedback. Now to the specifics … and a few more questions:
1) Thank you, I appreciate the critique. The High Wisdom build is for Perception and scouting, plus later Gloom Strider Survival boost and the far-off Monk dip. Thought is sensing danger first and running away (especially if out scouting alone) to avoid the hit is better than soaking the damage of a hit. That is my untried theory anyway. Thoughts?
2) We haven’t had a Session 0 yet, so I don’t know what the rest of the party will bring to the table. My concept leans Scout. But if the rest of the party doesn’t include a tank, I may go Assassin. I’m thinking Swashbuckler needs a different concept. May be a build starting with a Drow …
3) Rogue all the way to 5, rather than just 4 for the ASI? Is the Uncanny Dodge Feature or the 3d6 Sneak attack the driver? I was sort of prioritizing level multiples of 4 for Feat/ASI.
4) Prioritize Dex ASI bumps, check.
5) I am convinced to go Gloom Stalker for this build
6) The Archery Fighting Style will be the plan if I stick with the Scout path. If I go with the Assassin path, I wasn’t sure what Fighting Style to go with. GWF doesn’t work with Finesse weapons for Sneak Attack, so I thought it was between Dueling and TWF. Dueling’s +2 damage plus a shield versus TWF’s chance at additional damage (1d6+4 with the shortsword and Dex 18). The longer-term plan of going Monk, which doesn’t allow for a shield, lead me to think TWF. But what is the scaling issue you are talking about?
7) Ranger Levels 1 to 5 , check.
8) So if Scout & Archery, then Sharpshooter before Dex 20; if Assassin, then Alert before Dex 20; and if Swashbuckler, then Mobility before Dex 20. Plus remember to pick up Blooming Blade, check
9) The Monk-Kensei is what struck me. For the Scout & Archery build, 3rd level Kensei’s Shot adds 1d4 damage to arrow shots (no Ki cost), and 6th level Deft Strike adds 1d6 (for a cost of 1 Ki) and counting attacks as if magical (no Ki cost). For the Assassin build, the 3rd level Agile Parry for +2 AC seemed good. The Way of Shadow powers seem neat, but you are right about the Ki cost.
10) Will have to look into Long Death, is that in SCAG?
11) New options to consider …
12) As per 8, but could replace Feat with 18 Wis.
13) A late dip in fighter is what I was thinking. Action surge at 2nd level was the prime idea. Although if I can work it, there is some nice synergy with some of the Battle Master’s Combat Superiority Maneuvers (e.g., Evasive Footwork Plus Skirmisher and Dread Ambusher, etc.)
14) How are you getting 6 attacks for the Assassin 7-Gloom Stalker 5-Champion 3? I can see 2 from Extra Attack and x2 for Action Surge, and plus 1 from Dread Ambusher for 5, but not 6. Unless Action Surge doubles the Dread Ambusher one additional weapon attack or you are including the TWF bonus action attacks or Monk unarmed attacks for 6? Or are you looking at the Am I missing something?

New questions
For the Scout-Archer build (which I will start calling “Sniper” build), I think Scout 4-Gloom Strider 5 is the base. The questions become 15) How to use the last 6 levels (more Scout, more Gloom Strider, Kensei dip, etc.)? and 16) what order to build (Rogue 1, Ranger 1-5, Rogue/Scout 2-?; Scout 1-4, Gloom Strider 1-5, +?; )?

For the Assassin build (which I will start calling “First-Strike” build) I think Assassin 5-Gloom Strider 5 is the base. The questions are then 17) How to use the last 5 levels (more Assassint, more Gloom Strider, add Fighter, etc.)? and 16) what order to build (Rogue 1, Ranger 1-5, Rogue/Assassin 2-?; Assassin 1-5, Gloom Strider 1-5, +?; )?


I don't have a lot of time right this second but I'll touch on a couple points.

3) I like Rogue 5 for a cutoff because the extra d6 sneak die and Uncanny Dodge is worth it IMO.
9) I'm not super familiar with the Kensei but it sounds neat.
10) Yes check it out. Temp hit points on a kill and a nice fear effect. It's level 11 ability is one of the strongest in the entire D&D but you wouldn't get there.
14) Yes if you Action Surge on your first turn, you can use Dread Ambusher again.
15) I'd probably end up taking more Rogue levels than anything. The Rogue class gets you nice features at almost every level. I would want Evasion for sure whether you go it from Monk or Rogue. Of course taking more Monk levels wouldn't be bad because you'll be ki starved. I think Ranger 5 would be plenty.
16) Starting Rogue gets you an extra skill. Starting Ranger gets you more weapons and medium armor/shield.

[PeteNutButter]

I'd recommend avoiding Monk. It doesn't add as much as you'd like it to.

Typical build is rogue 5/ranger 5/fighter 2-4 From there you advance rogue. You don't want more than 5 in ranger (I'd probably start ranger to 5), because ranger 6 is worst level in the game. Fighter only needs the two levels, but battlemaster or champion are always popular.

Instead of taking dex or SS at level 4, people often take elven accuracy boosting a 17 dex to a 18 and giving triple advantage. Stats would be better as 8, 17, 14, 10, 16, 8.

Lastly to generate that advantage assassin is popular with this multiclass. Advantage on all SIX attacks if you go first on round one, which is easy to do with dex and wisdom to initiative, is very strong.

ASIs> Elven Accuracy to take dex to 18 > SS > 20 dex.

That's just the cookie cutter build though. Going with scout would also work, but I'd think if you aren't going for advantage, there is no point in elven accuracy.

[CTurbo]

I agree about Elven Accuracy only being worth it if you have a sure fire way of having advantage on a regular basis.

I also agree about skipping Monk

[PeteNutButter]

Also I just realized that this is for OotA... Glooomstalker is very powerful in that campaign. That means starting ranger to 5 would be by far the most effective. So effective that your DM might hate you or just start putting light everywhere. You have super darkvision with invisibility to darkvision when light isn't around... in the underdark. lulz

[QuickLyRaiNbow]

Wisdom is pretty useful in OotA. There are quite a few things that force wisdom saves, and although the DCs aren't often that high the consequences for failure are obnoxious, especially early in the game.

[GTNE90]

I don't have a lot of time right this second but I'll touch on a couple points.

3) I like Rogue 5 for a cutoff because the extra d6 sneak die and Uncanny Dodge is worth it IMO.
9) I'm not super familiar with the Kensei but it sounds neat.
10) Yes check it out. Temp hit points on a kill and a nice fear effect. It's level 11 ability is one of the strongest in the entire D&D but you wouldn't get there.
14) Yes if you Action Surge on your first turn, you can use Dread Ambusher again.
15) I'd probably end up taking more Rogue levels than anything. The Rogue class gets you nice features at almost every level. I would want Evasion for sure whether you go it from Monk or Rogue. Of course taking more Monk levels wouldn't be bad because you'll be ki starved. I think Ranger 5 would be plenty.
16) Starting Rogue gets you an extra skill. Starting Ranger gets you more weapons and medium armor/shield.

3) Extra Sneak Attack does seem promising.
9) Yes, the synergies seem like they could be nice.
10) The 15 level limit strikes again
14) Cool, I wasn't sure about that
15) I may have a couple item to think about here. I'll probably do it in a separate post.

[GTNE90]

I'd recommend avoiding Monk. It doesn't add as much as you'd like it to.

Typical build is rogue 5/ranger 5/fighter 2-4 From there you advance rogue. You don't want more than 5 in ranger (I'd probably start ranger to 5), because ranger 6 is worst level in the game. Fighter only needs the two levels, but battlemaster or champion are always popular.

Instead of taking dex or SS at level 4, people often take elven accuracy boosting a 17 dex to a 18 and giving triple advantage. Stats would be better as 8, 17, 14, 10, 16, 8.

Lastly to generate that advantage assassin is popular with this multiclass. Advantage on all SIX attacks if you go first on round one, which is easy to do with dex and wisdom to initiative, is very strong.

ASIs> Elven Accuracy to take dex to 18 > SS > 20 dex.

That's just the cookie cutter build though. Going with scout would also work, but I'd think if you aren't going for advantage, there is no point in elven accuracy.
Thank you for more insights.

I am curious about why folks don't think 3-6 levels of Monk would be that useful.

As I was thinking of it, for three levels they would be able to use a bonus action to do a 1d4+4 attack in melee combat, would have unarmored AC of 17+, would get the +10ft movement (which helps the Scout Skirmisher), defelect missiles, and have the Kensei abilities which can treat a weapon as a Monk weapon for flurry of blows; add +2 to AC in melee; and add 1d4 to bow damage.

Adding up to the 6 levels would also give slow fall, increase the d4 to a d6 for melee and bow bonus attacks, add a stunning strike, bump up speed by +15ft, and add the Kensei abilities of treating weapons as magical for overcoming resistance and immunities.

These seem pretty good. The question is then the trade off of other features from levels in other classes.

[CTurbo]

Thank you for more insights.

I am curious about why folks don't think 3-6 levels of Monk would be that useful.

As I was thinking of it, for three levels they would be able to use a bonus action to do a 1d4+4 attack in melee combat, would have unarmored AC of 17+, would get the +10ft movement (which helps the Scout Skirmisher), defelect missiles, and have the Kensei abilities which can treat a weapon as a Monk weapon for flurry of blows; add +2 to AC in melee; and add 1d4 to bow damage.

Adding up to the 6 levels would also give slow fall, increase the d4 to a d6 for melee and bow bonus attacks, add a stunning strike, bump up speed by +15ft, and add the Kensei abilities of treating weapons as magical for overcoming resistance and immunities.

These seem pretty good. The question is then the trade off of other features from levels in other classes.

A few levels of Monk are good and do add a lot, but you'd be very limited with ki, and adding more classes just means it would be even longer before your build "comes online" all the way

You're talking about a 3 or 4 class multiclass build. It's be like after levels 10-12 before you even got to that last class. Rogue 2/Ranger 2/Fighter 2/Monk 2 is not going to be a very good level 8 character. You'd be decent at a lot of things but not great at anything. Same thing with a level 20 character that's Rogue 5/Fighter 5/Ranger 5/Monk 5 for example

[the secret fire]

I agree about Elven Accuracy only being worth it if you have a sure fire way of having advantage on a regular basis.

I also agree about skipping Monk

Elven Accuracy is quite useful for a Monk (Shadow) 6/Rogue x build that focuses on dominating the stealth game with PwoT and Skulker. The added mobility from Monk also plays extremely well with a mobile sniper concept, and Stunning Strike can function as a get-out-of-jail-free card for snipers who get caught by melee thugs. Ninja snipers are scary.

OP: with that starting WIS, a level or two in Cleric could be really good. A cleric dip mixes best with AT in my experience, as shield use + melee cantrips (and Shadow Blade) mix well or the one-attack-per-round Rogue.

[GTNE90]

I have as a Base Rogue (Scout) 4/Ranger (Gloom Strider) 5, and since we plan to play the character for 15 levels, that gives me 6 level of different classes to mix and match. The five combos (A-E) I am thinking of are:

A) 1 Scout, 3 Kensei, 2 Fighter:
Pro: Add 1d6 Sneak, Uncanny Dodge; Martial Arts (bonus attack with 1d4+3-5), Ki IFlurry of Blows), +10ft Move, Kensei Weapons (+2 AC in melee, +1d4 damage with bow), Deflect Missiles; 2nd Fighting Style (TWF), Second Wind, Action Surge
Cons: No ASI, No Evasion, less Sneak attack, No Slow Fall and other level 4-6 monk features

B) 4 Scout, 2 Fighter:
Pros: Uncanny Dodge, Expertise, Evasion, 4d6 sneak attack, and ASI; Fighting Style (TWF), Second Wind, and Action Surge
Cons: No Monk Package; Limited Fighter, less sneak attack, no Superior Mobility (+10ft), 1 less Feat/ASI

C) 6 Scout
Pros: Uncanny Dodge, Expertise, Evasion, 5d6 sneak attack, 2 Feat/ASI, and Superior Mobility (+10ft)
Cons: No Extra Fighting style, no second wind, no action surge

D) 6 Gloom Stalker
Pros: All the Gloom Stalker package features: Improved Favored Enemy Improved Natural Explorer , Iron Mind (Wisdom saves), extra known spells and spell slot (level 2 and 3), Feat/ASI, Land Stride, Hide in Plain Sight, and: Stalker’s Fury (reroll 1 miss per turn)
Cons: No more Scout, Kensei, or Fighter features

E) 3 Scout, 3 Fighter (Battle Master)
Pros: Uncanny Dodge, Expertise, Evasion, 4d6 sneak attack, and Battle Master (Combat Superiority die)
Cons: no Feat/ASI, no mobility, lower sneak attack, and no Kensei features

Thoughts?

It seems B, C, or E are the initial recommendations.

[GTNE90]

A few levels of Monk are good and do add a lot, but you'd be very limited with ki, and adding more classes just means it would be even longer before your build "comes online" all the way

You're talking about a 3 or 4 class multiclass build. It's be like after levels 10-12 before you even got to that last class. Rogue 2/Ranger 2/Fighter 2/Monk 2 is not going to be a very good level 8 character. You'd be decent at a lot of things but not great at anything. Same thing with a level 20 character that's Rogue 5/Fighter 5/Ranger 5/Monk 5 for example

The Kensei isn't a really intensive Ki build, but your other point is very valid.

[GTNE90]

Elven Accuracy is quite useful for a Monk (Shadow) 6/Rogue x build that focuses on dominating the stealth game with PwoT and Skulker. The added mobility from Monk also plays extremely well with a mobile sniper concept, and Stunning Strike can function as a get-out-of-jail-free card for snipers who get caught by melee thugs. Ninja snipers are scary.

OP: with that starting WIS, a level or two in Cleric could be really good. A cleric dip mixes best with AT in my experience, as shield use + melee cantrips (and Shadow Blade) mix well or the one-attack-per-round Rogue.

Another interesting alternative. But staying with the Mobile/Hiding Sniper build (Scout/Gloom Strider), does Cleric help much, or does it only help at the end of the dip?

[MrStabby]

Shadow monk/gloomstalker is pretty good and there is no reason not to add rogue there if you want it.

I would say monk to 6 for shadowstep is the first part - it gets you extra attack on the way. Then gloomstalker to 3 and rogue the rest of the way.

As you want to play a rogue you may want rogue levels a little earlier. If it is the flavour of rogue you want you could stop at level 1 (so much overlap between cunning action and monk abilities that one of the class strongest ability becomes relatively weak - shadowstep can cover dash and disengage parts for the bonus action)

[rbstr]

I don't like MCing more than two classes or delaying your first level 5 class more than you have to. Too many good things at level 5 in basically all classes to put it off more than 1 extra level, maybe 2 at most.

Yeah, put me in the camp that 1-4 levels of monk is pretty cool on most Rangers (less so Horizon Walker and Monster Slayer since they use the bonus action more for class features). Any monk archetype works.
But also the camp of rogue/monk doesn't work all that well except as a dip going either way.

AND also in the camp that mid/high-level ranger stuff is cooler than the white-room centric groupthink will tell you. The level 3+ spells can be really cool and the level 7 and 11 archetype features are usually great.

[Talionis]

I was thinking of making a Rogue character with a Perception & Stealth focus, maybe leading to the Scout Archetype, but am open to others (Assassin and Swashbuckler being prime). I was considering dipping into Ranger for 3-5 levels for the Gloom Strider Archetype features and Extra Attack options, and maybe also dipping into Monk for 3-6 levels for the Kensei Archetype features. A dip into Fighter for 2 levels for a second fighting style and Action Surge are also possible....


Questions & Answers:
1) What do you think about the above draft build? I like to look at my final version and then look back again, so until you answer where you want to end up, its hard to say if you started out correctly.

2) What do you think about a Rogue(Scout), compared to Rogue(Assassin) or Rogue(Swashbuckler)? With out crazy stats, I would stay away from Swashbuckler, since Swashbuckler needs Charisma to be fairly high to work and you are also trying to put significant points in Wisdom, so you can't be that spread out and reach full potential. The Alert Feat can replicate most of the early benefit of Swashbuckler; and I do like Swashbuckler very much just not for the direction you are going. Scout is great for archers and scouts, so if that's what you want then fine. For optimization, Assassin is probably the best. GloomStalker and Fighter Action Surge do a whole lot to make you awesome in a surprise round. You didn't mention Arcane Trickster or Thief and both merit thoughts. Arcane Trickster can add some spells to your Ranger casting slots, which may have some very good inclusions. Find Familar comes to mind as being very appropriate, but there are a lot more. Thief is amazing in being able to handle objects with your bonus action, that can be so many things and upper story work makes you fairly mobile, so Thief can be a very well rounded choice. Rogue has a lot of great choices, which can make it hard.


3) Should I plan to go to Rogue Level 3 (for the Archetype features) or Level 4 (for the Feat/ASI) before changing class? Again, look at where you want to go. Even if you are a Rogue, getting Extra Attack somehow should be a priority because you want to try to ensure that you get your sneak attack off each round and more attacks help with that. I don't think ASI's are a huge priority for you. With your draft, you will be putting off your ASI's a lot. But if it were me, I would go 1 Rogue/ 5 Ranger/ 4 Rogue/ 2 Fighter/ X Rogue.

4) If 4th level Rogue, what is your opinion on taking the ASI on Dexterity or the Sharpshooter Feat? I like boosting Dexterity fast, because it benefits a lot of little things significantly.

5) What do you think about the Ranger(Gloom Stalker) compared to the Ranger(Hunter) or Ranger(Monster Slayer) or other Ranger archetype? You pick, but if you are doing the opening round damage, then Gloom Stalker is great. Gloomstalker also helps you to stealth in darkness... Its a great. The others are good, but you'd need to say you want to go in those directions. I think your design lends itself to Gloom Stalker


6) I was thinking the Archery fighting style, or does the two weapon fighting style seem better, or does it depend on the party mix (tank or not)? Any of them work. Archery is better than throwing weapons. The buff to accuracy helps you to guarantee hitting for Sneak Attack each round and it later helps to offset Sharp Shooter. Archery won't help with Throwing weapons, but they are good if you plan to melee some. Thrown weapons are not really a fighting style that is highly supported currently in 5E. But with your design you can make it work fine. One level of Monk, can be useful here to get some slightly stronger thrown weapons to key off of Dexterity like the Hand Axe and the Light Hammer.


7) Should I plan to go to Ranger Level 3 (for the Archetype features), Level 4 for the Feat/ASI), or Level 5 for the 2nd Attack before changing class? Level 5. This is probably where you are going to get Extra Attack. The ASI will come at a good time. You can safely leave and forget Ranger after Level 5.

8) If 4th or higher Ranger, what is your opinion of taking the ASI on Dexterity, Sharpshooter Feat (if not chosen previously), or the Alert Feat? You'll want all three, but do Dexterity first, because it will help you to hit when you start using Sharpshooter. Alert is a good pick up eventually, but Dex does a little of what Alert does anyway, so best to get the broader Dex bonus first.


9) What is your opinion on the second dip/dive into Monk levels, versus more Rogue or Ranger, or going Fighter? This is going to be a personal preference. As above, one level of Monk can be very neat if you want to throw hammers or axes... The unarmored defense is also nice and this might be a good one level dip that you might even start your character with. Ranger is fairly weak after level 5, so I'd stop there, but getting Extra Attack early in your career should be a priority. Fighter, is probably icing on the cake... Its unnecessary to the build, but can flesh out the build at some point... Action Surge is more a priority if you are going to go for the Gloomstalker 3/ Fighter 2/ Assassin 3/ X build that wants to concentrate on very good surprise rounds...


10) What do you think about Monk(Kensei), compared to Monk(Way of Shadows) or Monk (Open Hand) or other Monk archetype/tradition? This is going to be your choice... I like the one level dip in Monk, maybe early in the build, but I see little value in a bigger dip. You may not have enough Wisdom to make Open Hand pushes work well. Shadows has great features at level 6. I am away from XGtE right now so I am less sure where the break points on Kensai are, but I remember wanting a lot of levels in Kensai too. Monk is a class that is really hard to dip because you get Ki point choked where you wish you had more Ki. So I suggest for your build, one level if at all. But I do like that initial level, I think it brings a lot to your table. In variably you will get in spot where you lose your armor and even if you haven't maxed Wisdom, you'll probably max Dex and get some Wisdom modifier to help, but keying some of the Strength weapons off Dexterity is great for a build that is definitely not investing in Strength.


11) If I add Monk, should I go to Level 3 (for the Archetype features), level 4 (for the Feat/ASI), Level 5 (for extra attack if didn’t already in ranger, and other features), or Level 6th (for the Archetype features)? Level 1 or Level 6. The better Monk features tend to be at level 6 and that gives you some Ki points to work with. But I will suggest 1 level of Monk or no levels of Monk. -- If you do decide to go Monk 6, then Ranger 3 is enough.


12) If 4th level or higher Monk, what is your opinion of taking the ASI on Dexterity (if not already maxed), the ASI on Wisdom or another ability, the Sharpshooter Feat (if not chosen previously), the Alert Feat (if not already taken), or another Feat? See above. Max Dexterity first. Certainly look at maxing Wisdom too now, which will eat up a lot of your ASI's. Shadow doesn't need to max Wisdom, so if that is the direction, you may have room to add more feats. Because of the many dips you are looking at doing, you'll likely want to stay away from heavy investment in Monk because of how Monk likes high Dexterity and Wisdom and you'll be making it hard to get ASI's with all the dips.


13) If haven’t used up the 15 level, where do you think the remain ones should be spent? Rogue for better sneak attack and features (uncanny dodge, expertise, evasion, etc.)? Ranger for extra spells and features (favored enemy, iron mind, etc)? Monk for features? A dip into fighter for a second fighting style and features such as Action Surge? Let's presume the 3 Rogue Assassin/3 Gloomstalker/2 Fighter/6 Shadow Monk (14 levels -- that leaves 6 more) This is a nasty surprise round attacker that will be great at Scouting. One level of Fighter nets you Battlemaster, which could really be fun with this martial type of build. 2 more Rogue nets you Uncanny Defense, but you may not want to go farther since... You can get Evasion with Monk 7 and get Stillness of mind. So that is 5 Assassin/3 Gloomstalker/ 3 Fighter/7 Shadow Monk (18 levels)

14) Any other advice or thoughts? Once you know what you want, go back through and prioritize which levels to do first. With the build I showed for 18 levels you can easily pick up two more ASI's by putting another level in Monk, Fighter, or Ranger...

But on my similar character I did something unexpected, I did two levels of Knowledge Cleric so that when I sneak around I can know what I am seeing or accomplish a task without the rest of the group, you are so stealthy with combo of Shadow Monk and Gloomstalker this does come up. The few extra spells known is nice... Bless is a big one if you are using Sharpshooter Feat, too help offset the accuracy. Guidance is an excellent cantrip for a skillful character. If people ask me how I would build Batman in 5E this is my build: 5 Assassin/4 Gloomstalker/ 2 Fighter/7 Shadow Monk/ 2 Knowledge Cleric. Feats Crossbow Expert, Sharpshooter, ASI Dex, ASI Dex

Another feat you may want is Crossbow Expert since it can get you an extra attack in that opening round.

[the secret fire]

Shadow monk/gloomstalker is pretty good and there is no reason not to add rogue there if you want it.

I would say monk to 6 for shadowstep is the first part - it gets you extra attack on the way. Then gloomstalker to 3 and rogue the rest of the way.

As you want to play a rogue you may want rogue levels a little earlier. If it is the flavour of rogue you want you could stop at level 1 (so much overlap between cunning action and monk abilities that one of the class strongest ability becomes relatively weak - shadowstep can cover dash and disengage parts for the bonus action)

Both parts of the movement have to be in dim light or darkness. How much this restricts the ability's use is extremely campaign-dependent, but it can be a serious hindrance. Shadow Step gives a character with Cunning Action another option with the bonus action, but Cunning Action will still see a ton of use in normal play.

Also, OP said he is looking for "a Rogue character with a Perception & Stealth focus" and he's starting with high Dex and Wis. All of that screams out for Shadow Monk.

[Talionis]

the secret fire --

I actually agree that when I read the Op's intro I thought he wanted a bunch of Rogue, but the more I read his questions I began to think he wants a significant amount of Shadow Monk.

Shadow Monk is probably the easiest Way for Monks to multiclass. Non-maxed Wisdom is generally okay on a Shadow Monk, they don't need a lot of checks. They also don't need tons of Ki for their abilities.

Something of note is that if he multiclasses a lot, he may lose A LOT of his ASI's. So being careful to look at the cut offs and decide whether he really needs all the different multiclasses.

[MrStabby]

Both parts of the movement have to be in dim light or darkness. How much this restricts the ability's use is extremely campaign-dependent, but it can be a serious hindrance. Shadow Step gives a character with Cunning Action another option with the bonus action, but Cunning Action will still see a ton of use in normal play.

Also, OP said he is looking for "a Rogue character with a Perception & Stealth focus" and he's starting with high Dex and Wis. All of that screams out for Shadow Monk.

never played out of the abyss, but by repute it has a number of dark places out of the sun.

[the secret fire]

never played out of the abyss, but by repute it has a number of dark places out of the sun.

True...wasn't paying attention to the fact that OP is playing this character in an OotA campaign. Yeah, it's the underdark, so a perfect environment for a Shadow Monk...almost too good.

[GTNE90]

Shadow monk/gloomstalker is pretty good and there is no reason not to add rogue there if you want it.

I would say monk to 6 for shadowstep is the first part - it gets you extra attack on the way. Then gloomstalker to 3 and rogue the rest of the way.

As you want to play a rogue you may want rogue levels a little earlier. If it is the flavour of rogue you want you could stop at level 1 (so much overlap between cunning action and monk abilities that one of the class strongest ability becomes relatively weak - shadowstep can cover dash and disengage parts for the bonus action)

MrStabby -
I like the flavor of the Shadow Monk, but as CTurbo noted, the build is Ki point intensive isn’t it? At third level they can only cast 1 Shadow Arts spell per long rest, at fourth level they can cast up to 2 shadow art spells, and at sixth level the can cast up to 3 shadow art spells. If he gets to 6th level, then there is the nice synergy.

The other thing I’m not sure of is how effective the build will be along the way.

Assume I am targeting a Monk 7 / Ranger 3 / Rogue 5
1 Rogue Level 1
2 – 4 Ranger (Gloom Strider) Levels 1-3
5 – 10 Monk(Way of Shadow) Levels 1 -6
11 – 14 Rogue (Assassin) Levels 2-5
15 Monk(Way of Shadow) Level 7

It starts with the Expertise and Sneak Attack features, and picks up the Gloomstalkeer Magic, Dread Ambusher, Umbral Sight, and Primal Awareness features by 4 levels, but it is 8 levels before the first ASI, 9 levels before the Extra Attack, 10 Levels before the Shadow Step, 12 Levels Before Assassination …

I am not sure what a better build would be, or if the target should be tweaked to Monk 8/ Ranger 3/ Rogue 4 or something else.

[GTNE90]

I don't like MCing more than two classes or delaying your first level 5 class more than you have to. Too many good things at level 5 in basically all classes to put it off more than 1 extra level, maybe 2 at most.

Yeah, put me in the camp that 1-4 levels of monk is pretty cool on most Rangers (less so Horizon Walker and Monster Slayer since they use the bonus action more for class features). Any monk archetype works.
But also the camp of rogue/monk doesn't work all that well except as a dip going either way.

AND also in the camp that mid/high-level ranger stuff is cooler than the white-room centric groupthink will tell you. The level 3+ spells can be really cool and the level 7 and 11 archetype features are usually great.

rbstr -
So you would advocate:
1 Rogue Level 1
2 – 6 Ranger (Gloom Strider) Levels 1-5
7 – 15 Rogue (Scout) Levels 2 - 10
Versus:
1 Rogue Level 1
2 – 6 Ranger (Gloom Strider) Levels 1-5
7 – 8 Fighter Levels 1 and 2
9 – 15 Rogue (Scout) Levels 2-8
Or
9 – 12 Rogue (Scout) Levels 2-5
13– 15 Monk levels 1-3

The “white-room” vs “played” issue is a key question.

What are your thoughts on Sniper builds like:
Sniper
Rogue (Scout) 10 /Ranger (Gloom Stalker) 5: Max Sneak attack and extra ASI
Rogue (Scout) 9 /Ranger (Gloom Stalker) 6: Get Superior Mobility
Rogue (Scout) 8 /Ranger (Gloom Stalker) 7: Get Proficiency in Wisdom Saves
Rogue (Scout) 4 / Ranger (Gloom Stalker 11: Get Stalkers Fury
Rouge (Scout) 5 / Ranger (GS) 5/ Monk (Kensei) 3 / Fighter 2: Add Kensei Shot (+1d4 bow)& Action Surge
Rouge (Scout) 4 / Ranger (GS) 4/ Monk (Kensei) 5 / Fighter 2: 3 ASIs, Extra Attack, Kensei Shot (+1d4 bow)& Action Surge

[GTNE90]

Questions & Answers:
1) What do you think about the above draft build? I like to look at my final version and then look back again, so until you answer where you want to end up, its hard to say if you started out correctly.

2) What do you think about a Rogue(Scout), compared to Rogue(Assassin) or Rogue(Swashbuckler)? With out crazy stats, I would stay away from Swashbuckler, since Swashbuckler needs Charisma to be fairly high to work and you are also trying to put significant points in Wisdom, so you can't be that spread out and reach full potential. The Alert Feat can replicate most of the early benefit of Swashbuckler; and I do like Swashbuckler very much just not for the direction you are going. Scout is great for archers and scouts, so if that's what you want then fine. For optimization, Assassin is probably the best. GloomStalker and Fighter Action Surge do a whole lot to make you awesome in a surprise round. You didn't mention Arcane Trickster or Thief and both merit thoughts. Arcane Trickster can add some spells to your Ranger casting slots, which may have some very good inclusions. Find Familar comes to mind as being very appropriate, but there are a lot more. Thief is amazing in being able to handle objects with your bonus action, that can be so many things and upper story work makes you fairly mobile, so Thief can be a very well rounded choice. Rogue has a lot of great choices, which can make it hard.


3) Should I plan to go to Rogue Level 3 (for the Archetype features) or Level 4 (for the Feat/ASI) before changing class? Again, look at where you want to go. Even if you are a Rogue, getting Extra Attack somehow should be a priority because you want to try to ensure that you get your sneak attack off each round and more attacks help with that. I don't think ASI's are a huge priority for you. With your draft, you will be putting off your ASI's a lot. But if it were me, I would go 1 Rogue/ 5 Ranger/ 4 Rogue/ 2 Fighter/ X Rogue.

4) If 4th level Rogue, what is your opinion on taking the ASI on Dexterity or the Sharpshooter Feat? I like boosting Dexterity fast, because it benefits a lot of little things significantly.

5) What do you think about the Ranger(Gloom Stalker) compared to the Ranger(Hunter) or Ranger(Monster Slayer) or other Ranger archetype? You pick, but if you are doing the opening round damage, then Gloom Stalker is great. Gloomstalker also helps you to stealth in darkness... Its a great. The others are good, but you'd need to say you want to go in those directions. I think your design lends itself to Gloom Stalker


6) I was thinking the Archery fighting style, or does the two weapon fighting style seem better, or does it depend on the party mix (tank or not)? Any of them work. Archery is better than throwing weapons. The buff to accuracy helps you to guarantee hitting for Sneak Attack each round and it later helps to offset Sharp Shooter. Archery won't help with Throwing weapons, but they are good if you plan to melee some. Thrown weapons are not really a fighting style that is highly supported currently in 5E. But with your design you can make it work fine. One level of Monk, can be useful here to get some slightly stronger thrown weapons to key off of Dexterity like the Hand Axe and the Light Hammer.


7) Should I plan to go to Ranger Level 3 (for the Archetype features), Level 4 for the Feat/ASI), or Level 5 for the 2nd Attack before changing class? Level 5. This is probably where you are going to get Extra Attack. The ASI will come at a good time. You can safely leave and forget Ranger after Level 5.

8) If 4th or higher Ranger, what is your opinion of taking the ASI on Dexterity, Sharpshooter Feat (if not chosen previously), or the Alert Feat? You'll want all three, but do Dexterity first, because it will help you to hit when you start using Sharpshooter. Alert is a good pick up eventually, but Dex does a little of what Alert does anyway, so best to get the broader Dex bonus first.


9) What is your opinion on the second dip/dive into Monk levels, versus more Rogue or Ranger, or going Fighter? This is going to be a personal preference. As above, one level of Monk can be very neat if you want to throw hammers or axes... The unarmored defense is also nice and this might be a good one level dip that you might even start your character with. Ranger is fairly weak after level 5, so I'd stop there, but getting Extra Attack early in your career should be a priority. Fighter, is probably icing on the cake... Its unnecessary to the build, but can flesh out the build at some point... Action Surge is more a priority if you are going to go for the Gloomstalker 3/ Fighter 2/ Assassin 3/ X build that wants to concentrate on very good surprise rounds...


10) What do you think about Monk(Kensei), compared to Monk(Way of Shadows) or Monk (Open Hand) or other Monk archetype/tradition? This is going to be your choice... I like the one level dip in Monk, maybe early in the build, but I see little value in a bigger dip. You may not have enough Wisdom to make Open Hand pushes work well. Shadows has great features at level 6. I am away from XGtE right now so I am less sure where the break points on Kensai are, but I remember wanting a lot of levels in Kensai too. Monk is a class that is really hard to dip because you get Ki point choked where you wish you had more Ki. So I suggest for your build, one level if at all. But I do like that initial level, I think it brings a lot to your table. In variably you will get in spot where you lose your armor and even if you haven't maxed Wisdom, you'll probably max Dex and get some Wisdom modifier to help, but keying some of the Strength weapons off Dexterity is great for a build that is definitely not investing in Strength.


11) If I add Monk, should I go to Level 3 (for the Archetype features), level 4 (for the Feat/ASI), Level 5 (for extra attack if didn’t already in ranger, and other features), or Level 6th (for the Archetype features)? Level 1 or Level 6. The better Monk features tend to be at level 6 and that gives you some Ki points to work with. But I will suggest 1 level of Monk or no levels of Monk. -- If you do decide to go Monk 6, then Ranger 3 is enough.


12) If 4th level or higher Monk, what is your opinion of taking the ASI on Dexterity (if not already maxed), the ASI on Wisdom or another ability, the Sharpshooter Feat (if not chosen previously), the Alert Feat (if not already taken), or another Feat? See above. Max Dexterity first. Certainly look at maxing Wisdom too now, which will eat up a lot of your ASI's. Shadow doesn't need to max Wisdom, so if that is the direction, you may have room to add more feats. Because of the many dips you are looking at doing, you'll likely want to stay away from heavy investment in Monk because of how Monk likes high Dexterity and Wisdom and you'll be making it hard to get ASI's with all the dips.


13) If haven’t used up the 15 level, where do you think the remain ones should be spent? Rogue for better sneak attack and features (uncanny dodge, expertise, evasion, etc.)? Ranger for extra spells and features (favored enemy, iron mind, etc)? Monk for features? A dip into fighter for a second fighting style and features such as Action Surge? Let's presume the 3 Rogue Assassin/3 Gloomstalker/2 Fighter/6 Shadow Monk (14 levels -- that leaves 6 more) This is a nasty surprise round attacker that will be great at Scouting. One level of Fighter nets you Battlemaster, which could really be fun with this martial type of build. 2 more Rogue nets you Uncanny Defense, but you may not want to go farther since... You can get Evasion with Monk 7 and get Stillness of mind. So that is 5 Assassin/3 Gloomstalker/ 3 Fighter/7 Shadow Monk (18 levels)

14) Any other advice or thoughts? Once you know what you want, go back through and prioritize which levels to do first. With the build I showed for 18 levels you can easily pick up two more ASI's by putting another level in Monk, Fighter, or Ranger...

But on my similar character I did something unexpected, I did two levels of Knowledge Cleric so that when I sneak around I can know what I am seeing or accomplish a task without the rest of the group, you are so stealthy with combo of Shadow Monk and Gloomstalker this does come up. The few extra spells known is nice... Bless is a big one if you are using Sharpshooter Feat, too help offset the accuracy. Guidance is an excellent cantrip for a skillful character. If people ask me how I would build Batman in 5E this is my build: 5 Assassin/4 Gloomstalker/ 2 Fighter/7 Shadow Monk/ 2 Knowledge Cleric. Feats Crossbow Expert, Sharpshooter, ASI Dex, ASI Dex

Another feat you may want is Crossbow Expert since it can get you an extra attack in that opening round.

Talionis—
Thank you for more insight!
1) Yes, the ‘Ground-Up’ versus ‘End-in-Mind’ approach. I am starting to get enough input that I might have an End character I can now describe.
2) I like all the different Rogue Archetypes, but for this game I think it is down to the Assassin and Scout. My decision might come down to how the game plays. If I can Snipe a good part of the time, I’ll go Scout, if I end up toe-to-toe too much, it will be Assassin.
3) Yes, I am seeing a 1 Rogue / 1-5 Ranger / X build makes sense, where X could be 2-Y Rogue or Fighter 1-2/2-Y Rogue or Fighter 1-2/Monk 1-3/Rogue 2-5 …
4) ASI = +2 DEX, Check.
5) Gloom Stalker, Check.
6) My intent will be Archery with the Scout or Dueling if Assassin based on how the DM plays underdark encounters and the makeup of the rest of the party. If I pick up a Fighter level or two later, I’m inclined to go TWF if Scout or Archery if Assassin.
7) Level 5 Ranger, Check.
8) Planned Order for a Sniper: +2 Dex/Sharpshooter/+2 Dex/Alert; planned order for a Assassin: +2 Dex/Alert/+2 Dec/…
9) If I go Monk, it will be to 3rd level for the Kensei features. I think Ranger 5 is set, unless the higher-level spells really grab me. The Fighter 2 level dip is really tempting, especially with the Assassin type
10) Check.
11) The Monk 6/Ranger 3 (or /Ranger 4 for the ASI) versus Ranger 5/Monk 3 added to Rogue is a tough call.
12) As per discussion for 8, Check.
13) I will only likely play this character for 15 levels, so I only have 1 level to add to your suggestion.
14) Yes, End-in-Mind is the issue. A Sniper vs a First-Strike build is still an open question

[the secret fire]

The other thing I’m not sure of is how effective the build will be along the way.

Assume I am targeting a Monk 7 / Ranger 3 / Rogue 5
1 Rogue Level 1
2 – 4 Ranger (Gloom Strider) Levels 1-3
5 – 10 Monk(Way of Shadow) Levels 1 -6
11 – 14 Rogue (Assassin) Levels 2-5
15 Monk(Way of Shadow) Level 7

I would recommend:

Rogue 1
Shadow Monk 1-6
Rogue 2-7
...then do whatever you want, probably either advancing as a Rogue or getting three levels of Ranger.

This way, you only delay your extra attack by one level.

[rbstr]

rbstr -
your options

I like option 1 best, yeah. But 2 levels to get action surge is very strong. Weigh it against the other stuff you could get. 2 rogue levels there gets you the archetype and another sneak attack die. 2 Ranger gets you wis save prof. But those also get you closer to other great stuff: Rogue 5 is very strong for uncanny dodge. 7 for Evasion.


What are your thoughts on Sniper builds like:
Sniper
Rogue (Scout) 10 /Ranger (Gloom Stalker) 5: Max Sneak attack and extra ASI
Rogue (Scout) 9 /Ranger (Gloom Stalker) 6: Get Superior Mobility
Rogue (Scout) 8 /Ranger (Gloom Stalker) 7: Get Proficiency in Wisdom Saves
Rogue (Scout) 4 / Ranger (Gloom Stalker 11: Get Stalkers Fury
Rouge (Scout) 5 / Ranger (GS) 5/ Monk (Kensei) 3 / Fighter 2: Add Kensei Shot (+1d4 bow)& Action Surge
Rouge (Scout) 4 / Ranger (GS) 4/ Monk (Kensei) 5 / Fighter 2: 3 ASIs, Extra Attack, Kensei Shot (+1d4 bow)& Action Surge
I like Ranger-heavy snipers since Lightning Arrow is just one of my favorite things. I'd maybe start rogue1 but otherwise mc after level 9. That's just me, it's probably not optimal.