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I'm planning a Rogue/Monk character, and I'm planning on being a highly mobile Monk who moves around the battlefield a lot, trying to get as many attacks as possible.

The Rogue subclass is going to be the Swashbuckler, mainly for the Fancy Footwork feature:

During your turn, if you make a melee attack against a creature, that creature can’t make opportunity attacks against you for the rest of your turn.

I do not know for certain which Monk subclass, but I am thinking of either Drunken Master for the free disengage when using Flurry of Blows (from Tipsy Sway) or Open Hand for the Open Hand Technique benefits.

I was planning on starting as Rogue and taking it to as least level three (for Fancy Footwork) then mainlining Monk to at least 5th, before going back to Rogue until at least level 12-13.

One of the ideas I had was to take the the Martial Adept feat, to add some variety to my actions.

I know some of the Battle Maneuvers aren't synergistic with monk abilities, like tripping, because Monks can eventually get Stunning Strike. The most important thing for my character is to be free to move between enemies, getting in as many attacks as possible, without being stopped or interrupted/killed.

Which maneuvers help with this the most?

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    \$\begingroup\$ The Drunken Master monk's "free" Disengage with Flurry of Blows comes from the 3rd-level Drunken Technique feature, not the 6th-level Tipsy Sway feature. That said, what's the benefit of that if you already have the Swashbuckler rogue's Fancy Footwork feature? (Is it just that you gain the benefit of Disengage against every enemy when you use Flurry of Blows, regardless of who you've attacked?) \$\endgroup\$ – V2Blast Sep 10 at 6:42
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Pure monk has more attacks with similar mobility

Rogue and monk don't multiclass very well

Rogues want a single, accurate attack. Monks want many attacks. Rogues gain a Sneak Attack die every other level. Monks gain a ki point (and thus a use of Flurry of Blows) every level. Rogues can Disengage as a bonus action for free. Monks can Disengage as a bonus action by spending a ki point. Rogues rely on Evasion at level 7 to survive area spells. Monks rely on Evasion at level 7 to survive area spells.

In the end, rogue and monk have both too much and too little in common to result in an effective multiclass. Ordinarily that would be fine - there's no need for every character to be minmaxed. However, combining rogue and monk prevents you from getting as many attacks as possible, while adding little to your mobility.

Attacks

If you go Rogue 3 / Monk 5, then you won't get Extra Attack until level 8. This conflicts with your desire to have as many attacks as possible. Even if you went Monk 5 before dipping rogue, each level of rogue you take is one less attack per short rest (by spending a ki point on Flurry of Blows).

Mobility

Base monk can spend 1 ki point to Disengage as a bonus action, using Step of the Wind. This costs you the two attacks you could have made with Flurry of Blows. Stunned enemies can't make opportunity attacks, so Stunning Strike also provides a (less reliable) way to escape.

Way of the Open Hand allows you to prevent an enemy from taking reactions (including opportunity attacks) when you hit them with Flurry of Blows. This doesn't reduce the number of attacks you can make, but does carry some risk - it doesn't work if you miss.

Way of the Drunken Master has Drunken Technique, which removes the risk entirely. You gain the benefit of Disengage when you use Flurry of Blows - no hit required. It also increases your speed by 10 feet.

If all that mobility isn't enough, you could take Mobile:

When you make a melee attack against a creature, you don't provoke opportunity attacks from that creature for the rest of the turn, whether you hit or not.

Unlike all of the other monk options, the Mobile feat works without spending any ki points. If you find yourself engaged by multiple enemies, you can make one attack against each one in order to escape safely - you don't even need to hit. Mobile also increases your speed by 10 feet.

Maneuvers

Unfortunately, you can only use one maneuver per short rest with the Martial Adept feat alone. If you prioritize mobility, then the Mobile feat is superior to any maneuver (including the mediocre Evasive Footwork). If you prioritize attacks hitting, then +2 Dex is your best bet.

The Riposte maneuver allows you to make a melee attack as a reaction when an enemy misses you with a melee attack. This grants you one additional attack per short rest, but if your goal is to increase your raw number of attacks, I would instead recommend the Sentinel feat.

Conclusion

Swashbuckler either comes online late or delays your Extra Attack. For optimal attacks and mobility, I recommend a pure Way of the Drunken Master monk without Martial Adept. If Drunken Technique doesn't give you enough mobility, the Mobile feat should fill any gaps. If you desire more attacks, the Sentinel feat will almost certainly provide you with more per short rest than Martial Adept.

If you want a Swashbuckler with additional attacks, I'd recommend a dip in Battle Master fighter instead of monk. Three levels gets you maneuvers (with way more maneuver dice), as well as a Fighting Style (Dueling or Two Weapon Fighting), medium armor, shields, and Action Surge1. Going to level 5 gets you Extra Attack.


1 Gives you an extra Sneak Attack if you use Ready. You can only get one SA per turn, but multiple in the same round.

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  • \$\begingroup\$ @DonFusili Correct, but you can combine Flurry of Blows and Disengage as a Drunken Master. I ended up condensing and clarifying that paragraph, though, so hopefully it's less confusing. \$\endgroup\$ – Red Orca Sep 10 at 13:52
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The obvious candidate: Evasive Footwork

When you move, you can expend one superiority die, rolling the die and adding the number rolled to your AC until you stop moving.

This is probably the best one on the list. A good roll on the superiority die can mean you are nearly untouchable for the duration of your move.

Honorable mention: Parry

When another creature damages you with a melee attack, you can use your reaction and expend one superiority die to reduce the damage by the number you roll on your superiority die + your Dexterity modifier.

If you do get hit while weaving between enemies, Parry allows you to reduce that damage a bit.

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    \$\begingroup\$ I like each of the answers. What I like best about this answer is that it directly answers the bottom line question with maneuvers that support the theme/concept; the focus is admirable. \$\endgroup\$ – KorvinStarmast Sep 9 at 18:02
  • \$\begingroup\$ Nice call on the Parry. Totally missed that one :) +1 \$\endgroup\$ – NautArch Sep 9 at 19:27
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You've got options!

Before I begin, I do want to note that the Martial Adept Feat only gives you one superiority die/short rest. This isn't going to be used all the time, so it's about when it can do the most for you because it's not happening all that often.

What you're describing is a character that is very good about moving around from creature to creature while striking as much as possible. It is difficult, if not really impossible, to balance both wanting to strike as much as they can and be able to move freely. The limited Bonus Action limits that choice.

Below you'll find a trio of ways to enhance your build in it's movement and attacks. Each style will do something a little bit differently, so it's very much up to you as to what 'sounds' most fun. You can try to make yourself a bit harder to hit as you travel, or you can extend your attacks to just one more target, or you can go pure damage optimization and try for one more sneak attack.

Movin' and Groovin': Evasive Footwork

When you move, you can expend one superiority die, rolling the die and adding the number rolled to your AC until you stop moving.

If you're trying to increase your strikes, then that most likely means you are utilizing your bonus action for Flurry of Blows. Without that bonus action for either a rogue's disengage or Step of the Wind, then you need something that will help you stay alive as you move and strike.

Caveat Emptor

My biggest concern here is as the game progresses, a d6 AC increase is going to get less attractive and be less meaningful as monsters get bigger to hit bonuses - unless the stats are amazing and the base character has a very good AC.

Batter up: Sweeping Attack

When you hit a creature with a melee weapon attack, you can expend one superiority die to attempt to damage another creature with the same attack. Choose another creature within 5 feet of the original target and within your reach. If the original attack roll would hit the second creature, it takes damage equal to the number you roll on your superiority die. The damage is of the same type dealt by the original attack.

While you can do this only once, it does add to the general idea of striking lots. With a hit, you'll get an automatic damage against another target within 5'. It does need a melee attack, but with the rogue , sounds like that's going to happen so you can sneak attack.

If you do go Swashbuckler, then just be aware that Fancy Footwork would only cover you against the primary target.

Moar damage: Riposte

When a creature misses you with a melee attack, you can use your reaction and expend one superiority die to make a melee weapon attack against the creature. If you hit, you add the superiority die to the attack’s damage roll.

This maneuver will let you attack as a reaction, which generally means off-turn. Which means you get another sneak attack (as long as it qualifies, but if you go swashbuckler, it could more likely). Do note, that just with your regular Action sneak attack, you'll need to use a finesse weapon in order to trigger the sneak attack damage.

The risk here is that if triggered, it means an enemy has engaged. Which may not be a situation you want to find yourself in (but still will, thanks DM!)

I also admit that this is not fully within the theme of the mobile multistriker. But it was really hard to pass up a maneuver that can be so impactful for a rogue.

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    \$\begingroup\$ Note, Sweeping Attack does not allow you to double dip on Fancy Footwork since you aren't making an attack against the second creature. \$\endgroup\$ – Thomas Markov Sep 9 at 17:07
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    \$\begingroup\$ @ThomasMarkov You still get it against the primary target, but true, it wouldn't extend the coverage. \$\endgroup\$ – NautArch Sep 9 at 17:10

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