How would you build the quintessential ninja?

[Ravinsild]

I want to play a Drow Rogue, but I want the quintessential “magical ninja” experience, maybe like a Nightblade from Elder Scrolls Online.

Highlights would be:

Stealth

Invisibility

Dual-Wielding and Ranged

Teleportation

Huge Burst/Nova



My initial instincts were Assassination Rogue 14/ Way of the Shadow Monk 6 for the Shadow Teleport but while it looks great on paper seems to be clunky in execution. You wouldn’t get Shadow Teleport until level 9 if you hit Rogue 3 and went immediately for it, and I’m just not sure it would be a fun experience the entire way through from level 1 to whenever.

How would you go about building your favorite version of our Japanese Assassin with mystical powers, suddenly appearing behind you from the shadows?

[Ignimortis]

I want to play a Drow Rogue, but I want the quintessential “magical ninja” experience, maybe like a Nightblade from Elder Scrolls Online.

Highlights would be:

Stealth

Invisibility

Dual-Wielding and Ranged

Teleportation

Huge Burst/Nova



My initial instincts were Assassination Rogue 14/ Way of the Shadow Monk 6 for the Shadow Teleport but while it looks great on paper seems to be clunky in execution. You wouldn’t get Shadow Teleport until level 9 if you hit Rogue 3 and went immediately for it, and I’m just not sure it would be a fun experience the entire way through from level 1 to whenever.

How would you go about building your favorite version of our Japanese Assassin with mystical powers, suddenly appearing behind you from the shadows?

Start VHuman with Mobile or Alert. Go Shadow Monk until you feel tired of it, I suppose a good point to drop out would be Monk 12, after which you can still go into Assassin Rogue, maybe until level 5 - you don't need to go further, I suppose, since you already have evasion. Then you might want to finish it off with Fighter 3, picking Battle Master for dirty tricks and Fighting Style and Action Surge for more burst.

P.S. Sorry, didn't notice you wanted to be Drow. Still works, though, but it would work best with a Wood Elf for extra Wisdom.

[CTurbo]

Assassin 11, Gloom Stalker 3, Shadow Monk 6

Would probably rather have Wood Elf than Drow since Gloom Stalker is going to increase your darkvision anyway and won't have the sunlight sensitivity problem. The Cha boost is a waste too.

So yeah it's take a while for this to come online but would be ridiculous once it does

[Ravinsild]

Assassin 11, Gloom Stalker 3, Shadow Monk 6

Would probably rather have Wood Elf than Drow since Gloom Stalker is going to increase your darkvision anyway and won't have the sunlight sensitivity problem. The Cha boost is a waste too.

So yeah it's take a while for this to come online but would be ridiculous once it does

I’m picking Drow for RP and aesthetic reasons, not trying to min/max.

I was just curious about the many builds and paths to realizing a Ninja-like build.

So far great responses though :)

[JellyPooga]

For a more mundane version of a ninja, I'm going to submit a pure Class Thief Rogue.

Fast Hands means you can use equipment like rope&grapple, smoke bombs and apply poison as a bonus action, bonus action Dash and Disengage means you're one slippery customer and Expertise in Stealth is essential (of course!), not to mention bonus action Hide.

Second Story Work is literally designed for rooftop shenanigans and being able to really shift while hiding is very ninja-ry. At higher levels, UMD gives you all the supernatural stuff you might want; Staves, Rods, Wands, Scrolls...all yours to play with, giving you functional access to every spell list, every spell level (so long as you have the gear).

And for a capstone, you get to move supernaturally fast; two turns in one round. Nice.

If Thief Rogue isn't a model for a "realistic" (non-supernatural) ninja, nothing is.

[Ravinsild]

For a more mundane version of a ninja, I'm going to submit a pure Class Thief Rogue.

Fast Hands means you can use equipment like rope&grapple, smoke bombs and apply poison as a bonus action, bonus action Dash and Disengage means you're one slippery customer and Expertise in Stealth is essential (of course!), not to mention bonus action Hide.

Second Story Work is literally designed for rooftop shenanigans and being able to really shift while hiding is very ninja-ry. At higher levels, UMD gives you all the supernatural stuff you might want; Staves, Rods, Wands, Scrolls...all yours to play with, giving you functional access to every spell list, every spell level (so long as you have the gear).

And for a capstone, you get to move supernaturally fast; two turns in one round. Nice.

If Thief Rogue isn't a model for a "realistic" (non-supernatural) ninja, nothing is.

B-but I asked for a more supernatural magical Elf kind of ninja build ideas ;-; I’m certain it’s somewhere between Arcane Trickster or Assassin and some amount of Monk with Way of the Shadows. Which is what several others spoke of, already. Just collecting ideas :)

[leogobsin]

Shadow Monk/Rogue is probably the right call, but I'd start with Monk and only go to Rogue once you hit 6. Feels like it gets you more 'ninja-y' stuff faster. Lets take a look at your highlights:

Stealth- Monk prioritizes good dex and has stealth as a class skill, plus Pass Without Trace. Once you start picking up Rogue levels, you can get Expertise in stealth, making you even better at it.
Invisibility- You don't get invisibility per se, but you've got Minor Illusion meaning you can always have something to hide behind, plus all the aforementioned stealth boosts
Dual-Wielding and Range- this is the one where Monk does admittedly fall behind. Martial Arts is at least as good as Two Weapon Fighting for damage though, and hand crossbows from being a drow helps your ranged options some.
Teleportation-Shadow Step is really the big draw for Shadow Monk: absolutely no cost, can be done every turn as long as its dark enough.
Huge Burst/Nove- Monk isn't the best here, but you've got lots of tools to get advantage between Stunning Strike, Shadow Step, and just simple being hidden.

[Ravinsild]

Shadow Monk/Rogue is probably the right call, but I'd start with Monk and only go to Rogue once you hit 6. Feels like it gets you more 'ninja-y' stuff faster. Lets take a look at your highlights:

Stealth- Monk prioritizes good dex and has stealth as a class skill, plus Pass Without Trace. Once you start picking up Rogue levels, you can get Expertise in stealth, making you even better at it.
Invisibility- You don't get invisibility per se, but you've got Minor Illusion meaning you can always have something to hide behind, plus all the aforementioned stealth boosts
Dual-Wielding and Range- this is the one where Monk does admittedly fall behind. Martial Arts is at least as good as Two Weapon Fighting for damage though, and hand crossbows from being a drow helps your ranged options some.
Teleportation-Shadow Step is really the big draw for Shadow Monk: absolutely no cost, can be done every turn as long as its dark enough.
Huge Burst/Nove- Monk isn't the best here, but you've got lots of tools to get advantage between Stunning Strike, Shadow Step, and just simple being hidden.

If this forum had a like button I would like your post.

[narvosa]

I am running a monk/wizard in my upcoming campaign. It is by no means min max but it has cool flavor and can has a lot of utility and control. Way of the shadow monk and bladesinger wizard. I plan on going to 6 for monk then dip two into wizard for bladesing. You have access to a ton of spells for ninja flavor. We are using a point by system so I am able to get away with 16 in dex 16 in wis and 16 in int while dumping str and a bit charisma. Plan on eventually taking wizard to 5 for level 3 spells like lightning bolt and fireball for cool ninja flavor.

[JellyPooga]

B-but I asked for a more supernatural magical Elf kind of ninja build ideas ;-; I’m certain it’s somewhere between Arcane Trickster or Assassin and some amount of Monk with Way of the Shadows. Which is what several others spoke of, already. Just collecting ideas :)

For a supernatural magical Elf ninja, I'd suggest Warlock. Maaaaybe with a little investment in Knowledge Cleric.

"What!?!" I hear you cry. "Why Knowledge Cleric JP?" Settle down young'un and I'll point out the full-spellcasting, the very lovely Thaumaturgy cantrip (distractions!) and best of all, the resourceless Detect Thoughts followed by a no-save Suggestion (such as "don't tell anyone about that weird feeling that your mind was being read you just had").

Warlock really speaks for itself, though. See in magical darkness, resourceless Invisibility, Jump[i] and [i]Disguise Self, Misty Step and Gaseous Form on the spell list...the benefits really make themselves apparent when you look at it with "Ninja" in mind.

[Ravinsild]

For a supernatural magical Elf ninja, I'd suggest Warlock. Maaaaybe with a little investment in Knowledge Cleric.

"What!?!" I hear you cry. "Why Knowledge Cleric JP?" Settle down young'un and I'll point out the full-spellcasting, the very lovely Thaumaturgy cantrip (distractions!) and best of all, the resourceless Detect Thoughts followed by a no-save Suggestion (such as "don't tell anyone about that weird feeling that your mind was being read you just had").

Warlock really speaks for itself, though. See in magical darkness, resourceless Invisibility, Jump[i] and [i]Disguise Self, Misty Step and Gaseous Form on the spell list...the benefits really make themselves apparent when you look at it with "Ninja" in mind.

So would you go hexblade for the traditional knife in the back assassination feel?

[JellyPooga]

So would you go hexblade for the traditional knife in the back assassination feel?

I'm not massively familiar with Hexblade, but from what I do know of it...no. Hexblade feels too combative for my conception of a Ninja at least.

I would go Archfey, probably Pact of Tome. Fey Presence feels like it fits for a quick distraction to make a getaway and is in-keeping with a "sudden surprise" style of ninja. Misty Escape needs no further explanation. Beguiling Defences doesn't seem too ninja-ry, but it's a nice defence either way. Dark Delerium, plunging a foe into a realm of fear and shadows...do I really need to explain how that fits into a ninja feel? Add to that a solid list of expanded spells; Sleep, Phantasmal Force, Greater Invisiblity and Seeming all fit the ninja theme. Tome Pact gives you valuable Cantrips; Thaumaturgy, Guidance, Message, Dancing Lights and Mending topping the list for me, at least (going solely by the PHB).

Great Old One also has a lot going for it as well; telepathy has obvious use in group infiltration, but more pertinently, Dissonant Whispers, Detect Thoughts, Phantasmal Force, Clairvoyance, Sending and Telekinesis on that Explanded Spell List are shoe-ins for the theme.

The Warlock may not have the best Nova damage, but when I think "Ninja" I don't think of someone great in combat, I'm thinking of someone that uses fear, misdirection and stealth as their primary weapons. Warlock accomplishes that at least as well, if not better than most other options.

[Ravinsild]

I'm not massively familiar with Hexblade, but from what I do know of it...no. Hexblade feels too combative for my conception of a Ninja at least.

I would go Archfey, probably Pact of Tome. Fey Presence feels like it fits for a quick distraction to make a getaway and is in-keeping with a "sudden surprise" style of ninja. Misty Escape needs no further explanation. Beguiling Defences doesn't seem too ninja-ry, but it's a nice defence either way. Dark Delerium, plunging a foe into a realm of fear and shadows...do I really need to explain how that fits into a ninja feel? Add to that a solid list of expanded spells; Sleep, Phantasmal Force, Greater Invisiblity and Seeming all fit the ninja theme. Tome Pact gives you valuable Cantrips; Thaumaturgy, Guidance, Message, Dancing Lights and Mending topping the list for me, at least (going solely by the PHB).

Great Old One also has a lot going for it as well; telepathy has obvious use in group infiltration, but more pertinently, Dissonant Whispers, Detect Thoughts, Phantasmal Force, Clairvoyance, Sending and Telekinesis on that Explanded Spell List are shoe-ins for the theme.

The Warlock may not have the best Nova damage, but when I think "Ninja" I don't think of someone great in combat, I'm thinking of someone that uses fear, misdirection and stealth as their primary weapons. Warlock accomplishes that at least as well, if not better than most other options.

The quintessential ninja I’m talking about is the one that Japan has taken into its pop culture which is very much direct hand to hand combat. Dagger in the neck kind of direct assault stabbing kind. I’ve never seen Naruto, but they’re prominent in several anime and OVA, and they’re more like potent burst damage ambushers than dark magicians.

Google “anime ninja” and almost all of the images are people with short swords, and a few with string weapons and claws and a few with the sickle on the end of a chain. The mystical aspect is more for gap-closing and escaping but the bread and butter is in martial prowess via weapons.

[bc56]

In that case, I would make a recommendation of more levels in gloom stalker. At 11 they get an extra attack if they miss, and at 15 they can dodge especially well. I would recommend drow high magic if you want supernatural senses, and definitely the athlete and mobile feats. Elven accuracy would also be very good. I would recommend at least 3 levels in arcane trickster or assassin to round it out and give it a backstabbing feel.

[JellyPooga]

The quintessential ninja I’m talking about is the one that Japan has taken into its pop culture which is very much direct hand to hand combat. Dagger in the neck kind of direct assault stabbing kind. I’ve never seen Naruto, but they’re prominent in several anime and OVA, and they’re more like potent burst damage ambushers than dark magicians.

Google “anime ninja” and almost all of the images are people with short swords, and a few with string weapons and claws and a few with the sickle on the end of a chain. The mystical aspect is more for gap-closing and escaping but the bread and butter is in martial prowess via weapons.

If that's the feel you're looking for, then I stick by my original suggestion of pure-class Thief Rogue. As you point out yourself, while Shadow Monk feels right, it's a very clunky build; unappealingly MAD (you want Dex, Con and Wis high, minimum, Str doesn't really want a dump for Athletic purposes if nothing else and Cha is very nice for social infiltration and obfuscation) and it all comes online somewhat later than might be desired.

Thief Rogue has pretty much everything it needs to really feel like a ninja from level 3 when it gets its Archetype. It may not be magical, but it can certainly appear magical. Invisibility is only the art of going unseen, teleportation is merely moving faster or more unexpectedly than the the mind can comprehend; good use of mundane equipment and high skills can achieve this and that's exactly what the Thief Rogue is best at. Just run two sample characters through some "Ninja encounters" at various levels and see who does it better; your originally proposed Assassin/Shadow Monk or a straight Class Thief. Until very high levels (maybe level 12-15+) my money is on the Thief in basically everything except a straight, extended (i.e. more than one or two rounds) fight in the dark, assuming appropriate equipment is available.

If you really want to focus on the combat aspect, I would dip a little Battlemaster Fighter; Action Surge and Superiority Dice/Maneuvers add a lot to what the Rogue has to offer with little investment. If you want shadowy magical stuff, then a Warlock dip gives a lot in that for again, relatively low investment. Fighter 3/Warlock 3 gives you a similar package to Shadow Monk 6, but it also offers less redundancy (e.g. Step of the Wind vs. Cunning Action) and greater flexibility to specialise your concept exactly the way you want it.

[willdaBEAST]

The quintessential ninja I’m talking about is the one that Japan has taken into its pop culture which is very much direct hand to hand combat. Dagger in the neck kind of direct assault stabbing kind. I’ve never seen Naruto, but they’re prominent in several anime and OVA, and they’re more like potent burst damage ambushers than dark magicians.

Google “anime ninja” and almost all of the images are people with short swords, and a few with string weapons and claws and a few with the sickle on the end of a chain. The mystical aspect is more for gap-closing and escaping but the bread and butter is in martial prowess via weapons.

You've expressed your intention to build a mystical, larger than life ninja, so try not to take this as confrontational or "you're doing it wrong".

The question that arises for me though is, if ninja's bread and butter is in martial prowess via weapons, what are samurai? To me a pivotal part of ninjas is being a counterpoint to the martial focus and honor of samurai. In a 1 on 1 fight, a samurai should have no problem defeating a ninja. Through guile, stealth and not being as tied to a code like Bushido, the ninja has other advantages. I get that this is within the context of a fantastical setting and that realism isn't a priority, but to me there's a Yin and Yang relationship between samurai and ninjas that is fundamental to either's identity.

When I think ninja, it brings to mind: stealth, assassin, Tenchu, agility, hiding in plain sight (most ninja weapons are essentially farming tools and humble beginnings contrast them with the nobility of samurai), willingness to do anything to win a fight, but also avoiding any prolonged combat. As far as the more mystic stuff: walking on water (which is based on reality), disappearing in front of people (smoke bomb, or in some cases a log of wood) and killing people without touching them (sending drops of poison down a string from the ceiling onto a victim). Again that's my approach and more based in reality than is probably necessary. I would personally try to incorporate as much of that flavor as possible in hopes to distinguish my character from being a generic assassin.

[MrStabby]

My first thought was hexblade 1 (cha for main stat, and gives you a burst damage against a single target) then gloom stalker 5 (if you can get the revised ranger even better, this adds to your burst damage and works well with hexblade curse, gets you your martial prowess with second attack. Next rogue 1 for expertise and a bit of sneak attack. Then 2 more hexblade for more casting and access to spells like misty step, you already have pass without trace from ranger). 2 more levels of rogue then get you swashbuckler for more sneak attack and better initiative.

So by level 11 you can have expertise in stealth and deception with great charisma and ok dexterity which should be able to let you infiltrate anywhere. You have ok damage generally but kicking off a fight and spending resources let's you do nova damage like a badass. You get access to a number of great Warlock spells to flesh out the concept. Downside you have 1 ASI but with attacks based on cha, initiative based on Cha and all spells with saves based on cha this is less important. Levels 12 and 13 can each give ASIs if you want.

Gloom stalker and Warlock invocations make you a master of darkness.

[Ganymede]

How would you go about building your favorite version of our Japanese Assassin with mystical powers, suddenly appearing behind you from the shadows?

I'd work on my PC's background as a mobbed-up killer and criminal, then I'd take literally any class that grants "mystical powers," of which there are a lot of them.

[Ravinsild]

You've expressed your intention to build a mystical, larger than life ninja, so try not to take this as confrontational or "you're doing it wrong".

The question that arises for me though is, if ninja's bread and butter is in martial prowess via weapons, what are samurai? To me a pivotal part of ninjas is being a counterpoint to the martial focus and honor of samurai. In a 1 on 1 fight, a samurai should have no problem defeating a ninja. Through guile, stealth and not being as tied to a code like Bushido, the ninja has other advantages. I get that this is within the context of a fantastical setting and that realism isn't a priority, but to me there's a Yin and Yang relationship between samurai and ninjas that is fundamental to either's identity.

When I think ninja, it brings to mind: stealth, assassin, Tenchu, agility, hiding in plain sight (most ninja weapons are essentially farming tools and humble beginnings contrast them with the nobility of samurai), willingness to do anything to win a fight, but also avoiding any prolonged combat. As far as the more mystic stuff: walking on water (which is based on reality), disappearing in front of people (smoke bomb, or in some cases a log of wood) and killing people without touching them (sending drops of poison down a string from the ceiling onto a victim). Again that's my approach and more based in reality than is probably necessary. I would personally try to incorporate as much of that flavor as possible in hopes to distinguish my character from being a generic assassin.

The same way MMA fighters bread and butter is fighting but some specialize in a ground game and some specialize in striking.

All of them fight, but not all of them fight equally in the same ways.

You described pretty well what I mean by ninja anyway: they are highly trained killers with razor sharp technique and they can hold their own in any fight. However they appear from the shadows and strike all at once in one devastating blow and disappear. They strike then fade, hitting from different angles, sowing confusion instead of a head on rush and a prolonged man to man battle like a Samurai.

If you’re familiar with 40k it’s basically like they’re all space Marines but Blood Angels are Samurai and Raven Guard are ninja.

Not going to lie, I was heavily inspired by the miniature I wanted to use for my character:

https://www.games-workshop.com/en-US/Dark-Elves-Shadowblade

[willdaBEAST]

The same way MMA fighters bread and butter is fighting but some specialize in a ground game and some specialize in striking.

All of them fight, but not all of them fight equally in the same ways.

If you’re familiar with 40k it’s basically like they’re all space Marines but Blood Angels are Samurai and Raven Guard are ninja.

Not going to lie, I was heavily inspired by the miniature I wanted to use for my character:

https://www.games-workshop.com/en-US/Dark-Elves-Shadowblade

I guess I see more of a distinction, like samurai would be Ultramarines and ninjas Dark Elders, even though that's an imperfect analogy. That miniature is def cool looking.


You described pretty well what I mean by ninja anyway: they are highly trained killers with razor sharp technique and they can hold their own in any fight. However they appear from the shadows and strike all at once in one devastating blow and disappear. They strike then fade, hitting from different angles, sowing confusion instead of a head on rush and a prolonged man to man battle like a Samurai.
This I totally agree with. However, I think my personal approach for a ninja would be a lightning fast attack and if that doesn't incapacitate the opponent, immediate retreat. That does pose problems in a co-op team based game like DnD though.

[Ganymede]

I think my personal approach for a ninja would be a lightning fast attack and if that doesn't incapacitate the opponent, immediate retreat. That does pose problems in a co-op team based game like DnD though.

While that might be evocative of an assassination attempt on a rival daimyo, ninja are still real people that behave like any other. The ideal strategy for one particular type of mission does not have to be an idiosyncratic behavioral tick that must be done in all situations in order to avoid breaking theme.

[Arcangel4774]

I like warlock 7 as an alternative to shadow monk 6 with relentless hex similarly allowing you to teleport to your target.

[Grod_The_Giant]

Going a bit farther afield... How 'bout a Rogue 1/Nomad Mystic? Start with Nomadic Step (teleportation), Nomadic Chameleon (stealth), and Psionic Weapon (burst damage), and take Blind Spot as your first talent.

[Legendairy]

Also a bladesinger/rogue mix could work really well too, yes it would be mad, but rituals would cover a lot, cantrips help with damage and rogue sneak attack and expertise. Basically keep going rogue and could do AT and get things like shadow blade, bladesinger gives you decent defensive abilities.

Also I think warlock fits it, or an AT rogue/fighter(champion) with elven accuracy (still may want some warlock levels for smite-lite and seeing through ALL darkness). Something like hexblade 2/3-champ fighter 3 or 6 if you want extra attack and a feat then rogue x.

Edit: paladin/rogue can work too with Assassination and smites you can do some brutal things, it’s all in the eye of the beholder. I played a sorcadin-paladorc as an anime ninja type. I went with vengeance and shadow for the subclasses, gives you the same-ish set up as a warlock but more spells and more smites, vengeance/conquest/oathbreaker can all play well for what you are looking for but it boils down to flavor. Now this won’t have expertise in stealth but you can go invis and greater invis attack from a darkness you make and see in sooooo it’s perspective.

[Mortis_Elrod]

I could do it a couple ways. Some may have been suggested tho.

Gloomstalker 3/Shadow Monk 6/Thief Rogue 11. I like thief rogue over assassin. However an argument could be made for either. Swashbuckler might be good as well considering you lower the requirements for SA.

Soul Knife 10/Bladesinger 6/gloom stalker 4. This incorporates some psionic teleportation and the superior dual wielding of Soul knife and a bit more mystical ninja flavor. Its 8 spellcaster levels with 10 Mystic levels. with extra attack and the appropriate fighting style. You also get the benefit of favored of extra AC and movement speed from bladesinging. Revised ranger is better for this for obvious reasons but phb ranger is good too.

Kensai 17/gloomstalker 3. This is a little different. Gloomstalker and Stalker feat gives you enough stealth with High dex. But what this really does is give you insane movement speed and multiple attacks on the first turn without adding in too much magic. You can carry nothing but daggers if you want to, and ask your DM if either of the fighting styles (archery or two weapon) work for you, if any of them do its great for throwing daggers. Each one is doing 1d10 and potentially more with Kensai Shot, Deft Strike, Dread Ambsher, and Sharpen the blade. Unerring Accuracy is also really good here. Whats worthy to note though is that you also get all the cool later features of Monk (except perfect self and empty body). Its not any more mad than a regular monk option either and you see the results early.

Monk(Shadow/Kensai/Open Hand) 8/Gloomstalker 12. This is a slight variation on above. Its slightly healthier and potentially less damage but you have more magic at your disposal and you get Stalker's Flurry which is a better cheaper Unerring accuracy coming in way before the previous. the 3 monks who get the most would be open hnad shadow and kensai. Shadow since you have enough spells and such to save ki points or spell slots whichever you prefer as well as the teleport is thematic and useful on that first turn with advantage. Kensai because it gives more damage with deft strike and potentially a better weapon, Open hand becomes so much better with that extra attack you get on the first turn, especially if you are one of them grapple ninjas.


Shadow monk 18/ Fighter 1(2)/ Rogue 1(2). So Empty Body is amazingly useful. as is the other 17 levels of monk when put together. This is your dagger build, with amazing speed and constant invis. Astral Projection is also really useful, but that leaves you with little to work with the other 2 levels. Fighter 1 gives you some extra health and fighting style along with second wind thats about as useful as a fighting style in the grand scheme of things so ask your dm on how you rule thrown weapons and archery/two weapon fighting. Fighter 2 is action surge which is certainly useful. But compare to 1 level of Rogue which is expertise in stealth and thieves tools which is a bit more prudent on a ninja. Sneak attack is barely noticeable at this level but welcome. Cunning Action is maybe better then actions surge simply for Hiding on bonus action and saving ki. Still is worth mentioning as this is your Smonk 18/ x build and doesnt change much.


Thats about it though, theres some other ninja-like builds but i think i covered most of it. Monk/Rogue/Ranger are the desired classes to use here with few exceptions.

[Aaramis]

Shadow Monk X / Rogue Assassin 3.

The reasons are already covered above, but the key here is monk levels. All you need to really be an assassin is 3 rogue levels.

You could also go /Warlock 2, for the see invis thing mentioned above + Hex (flurry of blows + hex = 4d6 extra damage), but Monk is one of those classes where the more you multiclass, the weaker you get. Need to be careful there.