Monk/Rogue multiclass path: when and what to upgrade to create ninja character

[Lombra]

Well the title says it all: with 14/14 to DEX/WIS, how would you plan your character level up from 1 to 20 in order to keep him efficient at most of his levels?

Thanks to the help I got here, here's now the updated level-up path that in my opinion would work at its best:

Levels 1 to 6: Monk 1 to 6; Way of Shadows; Alert feat at character's level #4.

Taking the first six levels as a Monk helps with survivability, and grants the ability Shadow Step from Way of shadows. The Alert feat feels essential to get the most out of the Assassinate ability featured in the Rogue's Assassin archetype.

Levels 7 to 10: Rogue 1 to 4; Assassin archetype; Lucky feat at character's level #10.

Here might be the optimal break-point to start leveling up the rogue, this way Sneak Attack and Assassinate won't come online too late in the adventure. The Lucky feat is precious and helps compensate the lack of good ability scores when you really need it.

Levels 10 to 12: Monk 7 to 8; +2 DEX ASI at character's level #12.

You'll get Evasion which is very handy at those levels and now ability scores are getting a bit raised, don't really know if it's worth doing it at this point in the game but it's something.

Levels 12 to 14: Rogue 5 to 6;

Here you get two very intreasting rogue abilities: Uncanny Dodge, which will help a lot if the stealth set up can't be performed, and Expertise, which, in this case, will double the proficency bonus for STR and DEX based ability cecks.

Levels 15 to 20: Monk 9 to 14; +2 WIS ASI at character's level #17.

From now on Monk all the way, increasing Ki pool, walking on liquid and vertical surfaces with the Unarmored Movement improvement, you'll get the Cloak of Shadows ability, +2 WIS ASI and, in the end, Diamond Soul.

The basic idea of the character is that he wants to sneak attack the most of the times, and is going to look for stealth set ups in order to get the most out of the "Assassinate" feat.
He's a Tiefling (style choice that hurts the build, i know, but I think that it fits the theme pretty well) and he's in a party made up of a sorcerer, a wizard , a tempest cleric, and a rogue. The strategy is probably going to be: sorcerer and wizard blasting/buffing from behind, cleric tanking/supporting while my character and the rogue take down one enemy at the time trying to sneak-attack as often as possible.

By the way, my character might want to use poisons (it's not like an honoralble anime-warrior or things like that) and I struggle on finding any informations about them, if anyone knows any official things about poisons I'll be glad to read from him about it.

Feel free to help improving the upgrade path, it looks ok to me but I'm sure it can be further optimized :)

[JellyPooga]

For me, there's too much Monk and not enough Rogue...and the Rogue comes online way too late.

Lvl.1 : Monk (1)
Lvl.2 - Lvl.5 : Rogue (1-4)
Lvl.6 - Lvl.10 : Monk (2-6)
Lvl.11+ : Rogue (5-14)

Monk as your 1st level gives you tangible benefits over the alternative; better Saving Throws and an extra Tool Proficiency in exchange for a Skill Proficiency is a deal I'll gladly take.

Taking both Classes to level 7 creates Evasion redundancy and aside from getting more Ki Points and increasing Unarmed Damage by a marginal amount, Monk 7+ doesn't do you a large amount of favours. Monk 6 gets you everything you need from the Class.

Rogue 7+, on the other hand, gives you the option of going Arcane Trickster instead of Assassin...which I heartily recommend. The versatility of AT far outstrips the circumstantial opportunities of Assassin. Also; Magical Ambush is awesome for setting up combos.

[Citan]

Well the title says it all: with 14/14 to DEX/WIS, how would you plan your character level up from 1 to 20 in order to keep him efficient most of the times?

The basic idea of the character is that he wants to sneak attack the most of the times, and is going to look for stealth set ups in order to get the most out of the "Assassinate" feat.
Hi!

There are several builds in the forum that are made of this particular combination. :)
Such as this one (http://www.giantitp.com/forums/showthread.php?457592-Ninja-vs-ninja-%28vs-ninja-vs-ninja-%29) or that one (http://www.giantitp.com/forums/showthread.php?424810-Ninja-Builds).

Also, it's hard to give you feedback if we don't know how you envision your character.
Is it only a solo player or part of a group?
Is he a Monk in origin that underwent harsh training as a Rogue (emphasis on Monk martials)? Or a Rogue that has been accepted into a Monk order to complete his assassin training with darkness mastery (emphasis on Rogue)?

Without more info, only general tips. :)
You have only 20 levels.
Some abilities are redundant between both classes (namely Evasion).
Monk effectiveness heavily depends on ki pool, so you want a decent pool.

Several options of break point.
1) Monk 17 / Assassin 3: the easiest to build, but you lose a few interesting features.
2) Monk 14 / Assassin 6: one of my personal favorites. You still get Diamond Soul for protection and decent damage/mobility for your Flurry of Blows. You also get a good pool of ki to balance between shadow abilities and classic Stunning Strike. From Assassin, you get Uncanny Dodge and another Expertise.
3) Monk 9 / Assassin 11: your ki pool is somewhat limited, so you'll use it mainly for shadow abilities and nova Stunning Strike. You still get the hefty boost in mobility from level 9 (run on water and walls). The big drawback is the loss of "invisibility as an action", but imo you can manage without. In exchange, you get a decent boost damage (3d6 more than previous build) as well as Reliable Talent which pretty much ensure you will always enable your surprise nova (some could say it's overkill with Expertise but well), even when the conditions for Hiding and Sneaking are not perfect. This is a good build if you prefer being extra good at skill checks while maintaining a good damage.
4) Monk 6 / Rogue 14: very limited ki pool means you use it only for shadow abilities, and get even more SA damage, Impostor and Blind Sense. I would not recommend it because very limited ki pool means other useful abilities of Monk are a net loss and you lose several good features of Monk (ASI, Stillness of Mind, Water/Wall running, ki points), but it works.

As to how to build it, first go Monk up to 6, then immediately start Rogue (unless need for ASI) up to 3 (4 for ASI, 5 for Uncanny Dodge), then back Monk up to lvl 9 for better ki and movement, then finish as you want depending on your break point choice.

My 2 cents. :)

Monk 6 gets you everything you need from the Class.

Rogue 7+, on the other hand, gives you the option of going Arcane Trickster instead of Assassin...which I heartily recommend. The versatility of AT far outstrips the circumstantial opportunities of Assassin. Also; Magical Ambush is awesome for setting up combos.
While I strongly disagree on the bolded part for a mix between Shadow and Assassin, I agree on the fact that your concept could be achievable with a Shadow Monk 6 / Arcane Trickster 14. You lose on the surprise nova, but you get plenty of tricks to have fun with (although you could even wonder what point it is to dip Shadow Monk at this stage unless fluff reasons, other martials would be easier ;)).

[Lombra]

Jelly I see why would you prefer going for Arcane Trickster, but I'd rather keep the arcane things low on this character: he's in a team with a sorcer, a wizard, a cleric and a rogue. Sorry for not pointing that out immediatly. The main strategy is going to be sorcerer and wizard blasting from behind, cleric for utility and tankyness, while my character and the other rogue work together focusing on one target at a time in order to get sneak attacks very often. As far as the flavour for the class I'd like to keep it mainly monk, the damage on SA won't be massive, but as I said there's another rogue much more specialized in there.
Hope this comment helps you helping me xD

[Lombra]

Citan, I think I'll follow your advices, the second variant you posted seems pretty much what I was looking for, and thanks for the level-up strategy :)

[Citan]

Citan, I think I'll follow your advices, the second variant you posted seems pretty much what I was looking for, and thanks for the level-up strategy :)
My pleasure.
And indeed it's probably the right choice to go Monk main anyways if you already have a Rogue main.

Have fun!

[Nicodiemus]

If you're trying to maximize SA utility, did you think of rogue(swashbuckler) instead of assassin? Also provides you with a very monk-like disengage and bonus to initiative.

[Citan]

If you're trying to maximize SA utility, did you think of rogue(swashbuckler) instead of assassin? Also provides you with a very monk-like disengage and bonus to initiative.
Swashbuckler in itself is a good dip for any martial class, it's very true.
However, for this particular build, it may not bring so much.
1. The "disengage" bonus can be achieved with the "Mobile" feat which also further enhances speed by 10 feet. Furthermore, this build should manage most of the time to put AoO to disadvantage, since it relies heavily on using darkness against creatures without blindsense/darkvision.

2. The "initiative" bonus will depend on CHA, and on a Monk/Rogue build, it's very probable CHA will be 14 at most, maybe even dumped to 10. And, for a build planning surprise attacks, Alert will probably be on the priority list, with a +5 bonus. So bringing only a +0/1/2 would be nice but probably not worth the archetype.

Finally, a Monk 14 / Rogue 6 will get Expertise in Sneak and 4 ASI to max stats, with emphasis on DEX more than WIS (since using ki more for extra attacks and shadow than on Stunning Strike), so he can easily keep at least one ASI, maybe even two, to get Alert, Mobile, or both.

So, all in all, Swashbukcler, while being great for other builds, is subpar in this case.

[Lombra]

So I was looking trough the feats section of the PHB and some of them cought my interest, I would like to discuss them and see if they can be worth the ASI. Here are them:

-Alert
You get a +5 boost to initiative, you can't be surprised while concious and the hidden creatures that attack
you won'tget the advantage on the attack roll. This one seems pretty useful for the Assassinate feat.

-Lucky
You gain the chance to potentially change the odds of the fight three times per long rest, which seems
pretty cool to me.

-Mobile
10 feet of extra speed, the ability to dash over difficult terrain without any malus, and if you attack a creature
you shut down it's potential opportunity attack for this turn. The third ability looks cool, but maybe not worth
the ASI.

-Skulker
You can hide from a creature while lightly obscured (as a free action?), you keep yourself hidden even
after performing an attack, or casting a spell, and sight perception checks are not influenced by the
dim light condition. This one looks good because you are going to keep getting adavantage on the attacks
while hidden, but the fact that when lightly obscured you can try to hide may conflict with the shadow monk' s
cloak of shadows, but maybe it's worth an ASI? Probably works better for ranged-wepon based characters.

-Defensive duelist
The character is going to wield a shortsword, which means that with this feat his AC gets boosted by
his proficiency bonus (may be worth over a DEX ASI?).

In your opinions which among those are the best bang-for-your-bucks feats for the monk 14/rogue 6 build?

[Lombra]

If you're trying to maximize SA utility, did you think of rogue(swashbuckler) instead of assassin? Also provides you with a very monk-like disengage and bonus to initiative.
It looks cool, but the swashbuckler doesn't fit the character's flavour in my opinion :)

[Citan]

So I was looking trough the feats section of the PHB and some of them cought my interest, I would like to discuss them and see if they can be worth the ASI. Here are them:

In your opinions which among those are the best bang-for-your-bucks feats for the monk 14/rogue 6 build?

I'm not an expert about hide and seek in D&D 5e, far from it (I just know that Invisible is not sufficient to be Hidden ;)), nor Assassinate, so I'll let The Old Ones from the forum address correct me.

Alert: UIM, I'd say that "surprised" in D&D 5e means you get a free round before rolling usual initiative, so it may not be strictly required for you. Except for the part that, without it, you, the surprise Assassin, could actually be surprised!!

Lucky: nothing to say, it's THE feat great for anyone at anytime.

Mobile: contrarily to your feel, I'd say that the third benefit is actually the most important for you.
You're not as tanky as other martials, and, while you get solid defense features (Uncanny Dodge, Evasion) it still uses your reaction. So you will want to keep it for when an enemy actually attacks you.
Meanwhile, being a Monk, you will want to go to close contact. And maybe rush through tight enemy lines to get to a particular target. Normally, it would mean probably risking at least one AoO for your target, more if you have to pass by others (such as in tight corridors).
With 2 to 4 attacks a turn, you can safely attack your target and retreat, you could even "waste" an attack on someone so you can safely move around.
This also means that in many occasions, not risking AoO frees your bonus action to Dodge or Hide instead of Disengage (or just add attacks).
Hence Mobile being, for me, and in spite of already having great movement as Monk, one of the best feat for you. :)

Skulker: as you say, it's better for "classic" Rogues or other stealth ranged build. For you it's pretty much redundant or useless imo:
* again, as a Monk, you'll be in close contact most of the time (and your movement, especially with Cunning Action -and maybe Mobile-, means that situations where you can't melee attack your target will be very rare).
* as for "hide in lightly", it may be situationally useful, but if you plan on using shadow abilities as a basis it will be rarely enabled.

Defensive Duelist: this is always a pretty good feat, although its values come online late (since it relies on proficiency bonus). Also, you already get pretty strong reaction defense. So, a good choice, but maybe not the priority. :)

[Corran]

-Alert
You get a +5 boost to initiative, you can't be surprised while concious and the hidden creatures that attack
you won'tget the advantage on the attack roll. This one seems pretty useful for the Assassinate feat.
A feat tax for assassin unfortunately, the way assassination is based off initiative. Not a bad feat overall, it also kinda helps you a bit defensively if you decide to fight inside the darkness spell that you can cast as a shadow monk (I say a bit, as having cunning action you can hide successfully most of the times at the cost of your bonus action, however if you dont hide successfully or if you choose to spend your bonus action on sth else, enemies get disadvantage on attacks against you while you fight them inside magical darkness, and you still attack normally). If you want to focus on your assassination, is difficult to ignore this feat.


-Lucky
You gain the chance to potentially change the odds of the fight three times per long rest, which seems
pretty cool to me.
A very good feat overall and for everyone, but more so for assassins. Being able to apply that extra rolls to the all-important surprise attacks, but more importantly to your initiative roll (if you roll really low), is huge. I highly encourage you to include this feat in your final build, and the sooner you get it the better.


-Mobile
10 feet of extra speed, the ability to dash over difficult terrain without any malus, and if you attack a creature
you shut down it's potential opportunity attack for this turn. The third ability looks cool, but maybe not worth
the ASI.
A very nice feat. Works especially good for melee skirmisher builds, preferably with those that have access to BB. Are you a melee build? If not, avoid it. If yes, maybe you should still avoid it. Cunning action mitigates somewhat the need for mobile. The feat is still useful, but the competition is high and imo you have better reasons to avoid it than getting it. (Edit: Citan makes some good points about mobile which I didnt think of since I am not playing or theory crafting about monks often, or ever. Maybe it is a very good feat afterall)


-Skulker
You can hide from a creature while lightly obscured (as a free action?), you keep yourself hidden even
after performing an attack, or casting a spell, and sight perception checks are not influenced by the
dim light condition. This one looks good because you are going to keep getting adavantage on the attacks
while hidden, but the fact that when lightly obscured you can try to hide may conflict with the shadow monk' s
cloak of shadows, but maybe it's worth an ASI? Probably works better for ranged-wepon based characters.
Not as a free action. Skulker feat allows you to take the hide action if you are only lightly obscured, while other creatures can do so only if they are heavily obscured. Wood elves get a very similar racial feature (aka mask of the wild). While there is some redundancy with cloack of shadows, remember that you have cunning action so the benefits of this feat are more combat friendly (use bonus action instead of action). Still, this is not enough of a reason to spend a feat on it. You already have darkness to exploit in a lesser extent, and if you even can find a way to exploit light obscurement, then playing a wood elf would probably be your go-to (stat bonuses fit the build), so you would avoid the feat again. Take this feat if you use a ranged weapon and you can take the cunning action to hide with high frequency when inside combat.


-Defensive duelist
The character is going to wield a shortsword, which means that with this feat his AC gets boosted by
his proficiency bonus (may be worth over a DEX ASI?).
Competes with other uses of your reaction. And you are more of a skirmisher (assuming melee and not ranged) than a melee dps or tank. Avoid it.


In your opinions which among those are the best bang-for-your-bucks feats for the monk 14/rogue 6 build?
In general I find alert and lucky to be very good feats for any assassin build. The rest of your feats must complement your in-combat strategy, with which I am not very familiar since I am not very familiar with the monk class. Pumping dex by 2 can never be bad, and is one of the best stat bumps, as it affects so many things.

[Lombra]

Thanks Corran and Citan for the deep and helpful analysis on the feats, which is much more than I could get from my little experience :)