How to maximize Monk DPR?

Question

I tacked the question above at the end of this question, but realised that it's probably best to ask in a separate post altogether.

My current strategy for maxing Monk DPR is to take 3 levels of Ranger (grabbing Dueling, Hunter's Mark, and Horde Breaker), and wield a monk weapon (see details in the linked question). The other build I'm considering involves 3 levels of Fighter (Champion), for Dueling and Increased Crit Range (Action Surge is sweet, but only once per rest).

How do these compare, and are they the best options for increasing Monk DPR? If not, what's the best approach?

Two ideal, but not required, constraints:

1. no more than 3 levels taken outside of Monk (due to 1d10 Martial Art die and Quivering Palm)
2. increased DPR shouldn't be at the expense of AC/Wis (so, char should have 20 Wis/at least 18 AC by the end game, unless there's a reliable tactic to keep the character alive, given the decreased AC).

First level stats are 16 Dex/Wis (Wood Elf), 14 Con.

Answer 1

I have few ideas based on your criteria but the best option really boils down to the situations the party finds themselves in and how the party functions in combat. Because of that, I'll list some options and give the pros and cons of each.

Idea 1: Monk 17/Ranger 3

(Take Hunter's Mark, Dueling, and either Colossus Slayer or Horde Breaker)

Possible Damage: 4d10+4d6+[1d8(CS)]+24 for 3 hours (Attack, Extra Attack, Hunters Mark x4 (each weapon attack) [, and Colossus Slayer])

Pros:

• Up to 3 hours of use split into up to 1 hour increments 3 times per long rest.
• Even if you are out of ki and Hunter's Mark uses, you still get Dueling bonus to weapon damage.
• Bonus 1d8 if target is under its max HP, even if you don't have ki or Hunter's Mark. (If you take Colossus Slayer)
• You can hit 1 additional target for 1d10+7 each. (If you take Horde Breaker)
• Ranger class features are nice to have for adventuring.
• d10 hit die

Cons:

• Hunter's mark only recharges on Long Rests and might be ended earlier than intended if you fail a concentration check.
• You don't get the full effect on the first round. You need to use your bonus action to cast Hunter's mark which means you don't get your bonus unarmed or Flurry because it requires a bonus action, only your 2 attacks +2d6 (+1d8 if you have CS and target is below max HP).
• Every time your mark dies, you have to use your next bonus action to pick another mark.
• Because Hunter's Mark is a concentration spell, you risk losing the effect if you take damage.

Idea 2: Monk 17/Fighter 3

(Take Dueling and Battle Master or Champion)

Possible Damage: 4d10+1d8+24 up to 4 times between rests or you run out of ki. (Attack,Extra Attack, Flurry of Blows, 1 damage dealing maneuver)

Pros:

• Superiority Die and Ki recharge on a short rest.
• Maneuvers have utility effects (Battle Master)
• Dueling
• Action Surge gives high burst potential once per short rest. (6d10+1d8+38)
• Second Wind (though 4-13 HP isn't that much at level 20)
• Proficiency with 1 artisan's tools. (Battle Master)
• d10 hit die
• Increased Crit Range (Champion)

Cons:

• You only get 4 rounds of bonus 1d8 damage.

Idea 3: Monk 17/Rogue 3

(Take Assassin or Swashbuckler)

Damage Potential: 4d10+2d6+20 (Attack, Extra Attack, Flurry of Blows, Sneak Attack)

Pros:

• Bonus damage not reliant on recharge. Only have to worry about ki
• If you don't have advantage, you can still sneak attack the target if one of your other party members is in melee range.
• Expertise (double proficiency bonus in 2 skills)
• (Swashbuckler) Sneak attack if no one else is within 5 ft of you.
• (Swashbuckler) Add your Charisma to initiative (if you want)
• (Swashbuckler) Your target can't make AoO against you.
• (Assassin) Crit on surprised target for 8d10+4d6+20
• (Assassin) Proficiency with Poisoner's Kit for potentially more damage or other utilities.

Cons:

• Smaller hit die (d8).
• Smaller minimum damage potential.
• Monk weapon must be finesse. (Not too bad, just limits weapon choice.)
• Can't sneak attack with unarmed strike
• Very reliant on party placement

Answer 2

The Ranger class has the best addition to damage with Colossus Slayer, Dueling, and Hunter's Mark added to your attacks:

1. Monk weapon/Unarmed Strike (1d10) 5.5 damage
2. Hunter's Mark (1d6) 3.5
3. Dexterity 5
4. Colossus Slayer (1d8) 4.5
5. Dueling 2

On your first Monk Weapon attack (it should be a monk weapon or else it won't proc Dueling) you get 20.5 damage (Sum of List item 1 to 5).

On the Extra Attack, you get 16 damage (Sum of 1, 2, 3, and 5)

On your Flurry of Blows, you get 14 damage on both attacks (Sum of 1 to 3)

This all adds up to a grand total of 64.5 damage per round (or 64).

And these would be your total relevant stats:
Dex 20 (2 ASIs)
Wis 18 (1 ASI)
Con 14
HP 146 (10 + 16d8 + 3d10 + 40) all rounded up
AC 19 Feats: Warcaster (to help keep Hunter's Mark up)

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There is a case to be presented for taking Horde Breaker:

Assuming it always triggers, it'll add 12.5 damage (Sum of 1, 3, and 5) bringing the grand total to: 76 damage. That's great and all but there are more synergies which can be done only with Colossus Slayer which I will explain below.

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Colossus Slayer triggers once per turn

This means it can trigger off of Opportunity Attacks out of your turn even if it is within the same round.

There are a number of ways this can be done but the self-sustainable ways is by taking Feats that grant you attacks outside of your turn. Feats like Sentinel, Mage Slayer, and Polearm Master.

Personally, I'd say take Sentinel as it is the most consistent of the three and grants you OAs even if a creature uses Disengage.

One attack taken outside of your turn has the potential damage of 20.5 per turn, receiving the bonuses from Colossus Slayer (and possibly Hunter's Mark). Minor Note: it might have some synergy with the Tranquility feature, but that is merely a fringe case.

The problem with taking a feat is it lowers your AC, dangerously, to 18 as you would have to sacrifice increasing your Wisdom.

Answer 3

Monks get more damage by having more ki. More ki is obtained by getting more monk levels. Every level you take outside of monk means 1 (or more because of stunning strike) fewer hits landed per short rest.