I am playing a multiclassed wood elf with the Charlatan background; my class levels are Monk 6, Fighter 2, and Rogue 3.
Does this mean on my turn this can happen:
Attack 1:
Shortbow 2d6 + dex + 2d6 (Autocrit surprised, sneak attack)
Move 60ft. towards target
Attack 2 (Extra Attack from monk 5):
Unarmed 1d6 + dex
Flurry 1 1d6 + dex
Flurry 2 1d6 + dex
Disengage move 70 ft. away from target
Attack 3 (Action Surge from fighter 2):
Shortbow 1d6 + dex
Hide as a bonus action (Cunning Action from rogue 2)
Or would I add the sneak attack and autocritical to every roll because through my whole turn the target is surprised? Or is the target only surprised for the first attack?
I should mention that I have the Mobile feat, which is why my movement is 60 ft. – and I can move 70ft. and disengage for free after a Flurry of Blows due to the Drunken Master monk tradition. I autocrit because of the assassin archetype on rogue as well.
Best Answer
No
You only get 1 bonus action.
To do what you describe you need to use these Bonus Actions:
To clear up some misconceptions:
The Disengage action doesn't give you extra movement
You seem to think that Drunken Technique gives you extra movement after you use Flurry of Blows but it only increases your speed by 10 feet. Disengage merely prevents opportunity attacks.
To gain extra movement equal to your speed (70 feet after the Drunken Technique bonus) you need to take the Dash action.
Action Surge doesn't give you an extra bonus action
You used your bonus action on Flurry of Blows...
So you don't have a bonus action to hide at the end. Action Surge only grants an additional action, no extra bonus action.
Automatic criticals?
You do, however, get a critical hit on every attack that you hit since the target is surprised until the end of its first turn in combat. From the description of surprise:
Critical hits also double your Sneak Attack damage dice, so your Sneak Attack (whichever shortbow attack you apply it to) will do 4d6 damage, not 2d6.
You also have to go first or the target removes surprise before you get the chance to hit them (since it happens after their turn). There is no surprise round in 5e so the enemy rolls Initiative before your first turn (but gets no actions, reactions, or movement for that turn if they are surprised).
What you can do:
However, you can still get off your 5 attacks (and then some) with your build.
You just end up only 10 feet away and don't get to hide at the end.
You can only Sneak Attack once per turn (but all of your bow attacks qualify as opportunities to use it because Assassin gives you advantage):