D&D 5E Assassin/ninja build advice

[Snapdragyn]

I'm working on an assassin, or possibly assassin/ninja build, & would appreciate some char op feedback:


- Archery or Two Weapon Fighting build?
Archery would make it easier to get the drop in a surprise round, I think (aim & shoot vs. worrying about being able to get to a foe in time), but TWF doubles the chance of hitting (& thus getting in sneak attack damage) on a round.


- Multiclass Way of Shadows Monk?
It's cool, it helps with getting to a foe for melee build (with extra movement, plus Shadow Step with a deeper monk commitment), & I frankly don't care about the Assassin abilities past 3rd level - but it sacrifices sneak attack dice, & has the standard 'when do I take what class?' progression worry of any multiclass character. Maybe max out at 8 levels in monk around level 11 or 12?



Probably going half-elf for the Darkvision (hard to sneak around with a light source), decent stats, & extra skill (yes, even for a rogue). Story-wise, I'll say he's half-drow, although it won't have any game effect to distinguish him from any other half-elf. Criminal background w/ Spy variant & Cult of the Dragon Infiltrator variant background feature. Not nature-oriented, so Ranger dip was never an option.

 

[Zaruthustran]

What's your goal/vision when you say "ninja/assassin"?

If you're going for style points/theme, then it's hard to beat straight Monk (Way of Shadows).

If you're going for the ability to kill a target in one round (assassination), then it's hard to beat straight Rogue (Assassin).

If you decide to multiclass, I'd recommend Rogue 3, Monk 6, then Rogue the rest of the way. Shadow Step will ensure that you Surprise your target, and the sneak attack damage ensures that the target gets hurt real bad.

It's also worth considering at least 2 levels of Warlock for the standard combo of Darkness + Devil's Sight. With no need for Darkvision you can go human and grab that extra feat. If you go with 3 levels of Warlock (and Path of Chains) you can get an invisible Familiar, which means you'll always have an "enemy of the target within 5 feet of it" for sneak attack triggering. If you do go Warlock, I recommend Fey Pact because Sleep is amazing.