How many attacks and other techniques can I make with the actions I have as a multiclassed Monk 6/Fighter 2/Rogue 3?

Question

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.

Answer 1

No

You only get 1 bonus action.

To do what you describe you need to use these Bonus Actions:

1. Flurry of Blows unarmed strikes
2. Dashing with Cunning Action
3. Hide with Cunning Action

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.

If you take the Disengage action, your movement doesn’t provoke opportunity attacks for the rest of the turn.

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...

Immediately after you take the Attack action on your turn, you can spend 1 ki point to make two unarmed strikes as a bonus action

[emphasis mine]

So you don't have a bonus action to hide at the end. Action Surge only grants an additional action, no extra bonus action.

On your turn, you can take one additional action on top of your regular action and a possible bonus action

[emphasis mine; read the italicized portion as a single grouping]

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:

If you’re surprised, you can’t move or take an action on your first turn of the combat, and you can’t take a reaction until that turn ends

[emphasis mine]

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.

1. Attack action
   • Shortbow attack
   • Move into range (60 feet) for Extra Attack unarmed strike
2. Flurry of Blows
   • 2 unarmed strikes
   • Move away 10 feet with Disengage active (gained from Drunken Technique)
3. Action Surge: Attack action
   • Shortbow attack (2 if you want because of Extra Attack)
4. All attacks are made with advantage and those that hit are critical hits since the target is surprised.

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):

Once per turn, you can deal extra 1d6 damage to one creature you hit with an attack if you have advantage on the attack roll. 

[emphasis mine]

Answer 2

No. All of that cannot happen on a single turn.

tl;dr The action economy does not allow for the sequence as described. Specifically, too many bonus actions and misinterpreted disengage benefits.

Breakdown of Action Economy

On your turn you get one of each: action, move, bonus action, reaction

Shortbow 2d6 + dex + 2d6 (Autocrit surprised, sneak attack)

Correct: That consumes your action as Attack, and is 1 of 2 attacks provided by Extra Attack class feature.

Move 60ft. towards target

Correct: Wood elf base speed 35 + 15 unarmored movement (lv5) + 10 mobile feat gives you 60 total movement. This consumes 60' of 60' of your move.

Unarmed 1d6 + dex

Correct: This is the 2 of 2 Attacks provided by Extra Attack class feature.

Flurry 1 1d6 + dex and Flurry 2 1d6 + dex

Correct: This consumes your bonus and 1 ki to use flurry of blows.

Disengage move 70 ft. away from target

Incorrect: Drunken Technique (UA or XGtE) increases your movement by 10' and grants the benefits of disengage. You can move 10' feet away from the opponent at this point as only 60' of 70' has been used.

Disengage does not replenish the characters move capacity. It only allows the character to avoid attacks of opportunity.

Attack 3 (Action Surge Fighter): Shortbow 1d6 + dex

Correct: This should actually get you two attacks with the shortbow as the Extra Attack class feature applies again.

Hide (Rogue Bonus Action)

Incorrect: The bonus was already used for flurry of blows.

Assasinate Surprise

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?

This has already been answered, Yes here: Does the Rogue's Assassinate feature grant criticals on multiple attacks?

Answer 3

Not exactly, but mostly. You gain 1 more attack and deal way more damage, but you cannot move as fast and cannot hide.

Let us look at it step by step.

We assume the following:

• every attack hits
• the target enemy is surprised and has not taken a turn yet
• you are unarmored (for unarmored movement)

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1. You take the Attack action and you attack (and hit) once with your Shortbow. You have advantage on this attack and thanks to Assassinate it is an automatical critical hit. The damage would be 2d6+Dex piercing (Bow) plus since you had advantage you can use your sneak attack for an additional 4d6 (doubled since you critically hit).

Assassinate

Starting at 3rd level, you are at your deadliest when you get the drop on your enemies. You have advantage on attack rolls against any creature that hasn’t taken a turn in the combat yet. In addition, any hit you score against a creature that is surprised is a critical hit.

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2. You move to your target. Your movement speed is: 35ft (Wood Elf) + 15ft (unarmored movement) + 10ft (Mobile) = 60ft. You cannot add your Drunken Technique bonus, since you cannot take the Flurry of Blows bonus action, yet. (Must the Flurry of Blows attacks occur after the initial (and extra) attack?)

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3. You take your extra attack from your Attack action, which you get since you have more than 5 levels in Monk. This can be (but is not restricted to, see: Can any attack action trigger Flurry of Blows?) an unarmored attack. This is also a critical hit, thanks to Assassinate (see: Does the Rogue's Assassinate feature grant criticals on multiple attacks?). Thus dealing 2d6 + dex bludgeoning damage.

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4. Take your bonus action now for two Flurry of Blows attacks, each of which is also a critical hit and deals 2d6+dex bludgeoning damage.

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5. Since you are a Drunken Master you gain the benefit of the Disengage action and gain 10ft bonus movement. Thus you can only move 10ft, not 70ft.

Drunken Technique

At 3rd level, you learn how to twist and turn quickly as part of your Flurry of Blows. Whenever you use Flurry of Blows, you gain the benefit of the Disengage action, and your walking speed increases by 10 feet until the end of the current turn.

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6. Now you take your action surge, which you gain as a level 2 Fighter.

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7. You use your action surge for another Attack action granting you two additional attacks, since you have the Extra Attack feature. Thus you can attack twice with the Short Bow, each attack being a critical hit and dealing 2d6+dex piercing damage.

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8. You cannot hide now, since you already used your bonus action for Flurry of Blows and action surge only grants you an action, not a bonus action. (See: Does an Action Surge grant a second bonus action?)