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And it doesn´t seem to work when initiating combat, it has to be in the first turn, tried the assassin to see if I could get some sneaky crits by initiating ... that didn´t work.
So, the thief can just equip a second hand crossbow and pretty much get the same results by having an extra off hand attack, especially when initiating and retreating without getting caught.
But assassin 5/ gloom stalker 5/ warrior 2 let’s you have a monster turn one beating bake to make 7 attacks , all of which with advantage and all of which crits if you surprise the enemy . You get your opener stealth attack which doesn’t cost action if you open, then dread ambusher , then 2 normal attacks, then 2 more from action surge and one bonus if you have 2 crossbows .
That plus the naturally high initiative allows you to assassinate several opponents or even a major boss.
But yea it peaks at lvl 4-5 and you don’t get much more really good stuff after so best to multiclass it
You can always deep the ranger into thief 4 for the extra bonus action (+ feat) which allows to both dash and hide in the same turn ... or fire with bonus actions. The ranger doomstalker also gets that sweet first turn attack ... with double hand crossbows he can make 5 attacks in one round by level 8 with no help from potions or other spells/abilities. That´s with 3 thief and 5 ranger.
That said - most fights, you arent fighting 20 dudes. You are fighting 4-6 enemies. Assasin kills 1-2, guaranteed, at the start, using special arrow. Its all about that first hit, so you stack it up, and assasin kills the most dangerous enemy on the field. Job done.
That said. Most dangerous enemies on the field in act 3 are bane casters/monks, who have Unstoppable 5. So your 1st shot, and the subsequent 4 shots, go down the drain. Which is bullcrap by the way.
So, assasin is a bit of a wasted class.
You can build one as a hireling, and take him out for a spin for the one specific fight you need him. I cant think of any act 3 fights where turn 1 burst damage would matter, but in theory, hireling.
I do the same for stealing thief. i have a hireling rogue/bard (for cats grace and other self buffs), and i take him out when i need to rob merchants. Then back into the closet he goes. So you can do the same with assasin.
But....rogue is better. Extra action is OP.