Speedy Monk/Rogue (5e Optimized Character Build)
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To get the most out of this build, you need Sword Coast Adventurer's Guide.
This class combination is all about maximum maneuverability over a battlefield. You will have a high base move speed, easily doubled with cunning action.
The build doesn't actually have primary abilities, though wisdom and dex need to be 13 to multiclass as monk/rogue. A high dex is good for attack roles (although strength does work with sneak attack and unarmed attack) Higher wisdom would increase your AC.
- Alignment: With the apparent removal of a lawful alignment requirement for monk, any can work.
- Skills: Choose what you wish, and as a rogue you'll have a fair few choices. I suggest stealth, acrobatics, and athletics. With others as free choices.
Background choice is up to you. Choose one to fill in skills you want but couldn't get, or for a feature that you find interesting or of use to you in the campaign.
Race is interesting. Any will do. But Wood Elf is probably the best. +2 dexterity, +1 wisdom, dark vision, a base movement speed of 35 instead of 30(or 25 for halflings).
The reason for rogue is two fold(neither sneak attack, though it is nice.) First is Cunning Action. This grants Dash, Disengage, or Hide as able to use as a bonus action on your turn. This is important, as dash as a bonus action means you can move, attack, bonus action dash for your full move again. Monks do get the ability to do the same for dash and disengage, but it costs them a Ki point.
Second, and more important, is the swashbuckler archetype in Adventurers of the Sword Coast. You're only taking three levels of rogue, but that's all you need. You want Fancy Footwork, as this means when you make a melee attack, you can move away from the target without provoking an Attack of Opportunity from them. Rakish Audacity is nice as well, as it cuts down on the limitations of your sneak attack, making it better. And if you have a decent charisma you add your bonus from that to your initiative rolls. Which is nice, but not a selling point of this build.
Replacement in Unearthed Arcana
The bardic college of satire, in unearthed arcana: Kits of old, Allows the same "Cunning Action" style ability except it grants both dash and disengage at the same time. This build will need the "Mobile" feat to compensate for the loss of "Rakish Audacity" if Sword Coast is allowed.
Monk(and the rest, but at least 2)
Monk is what makes this build really shine. If you take this to 3 rogue/17 monk as a wood elf you'll have a base movement speed of 60ft when unarmored. With your dash as a bonus action you can move 120ft in a single round. So you can move 60ft, make two attacks(one from extra attack from monk levels), with a damage die of 1d10 and sneak attack dice of 2d6, then use your dash action to move another 60ft without provoking an opportunity attack from moving.
Levels 1 to 3: Rogue
You'll want to start off as a rogue, for the expanded proficiencies. And though not necessary, I suggest sticking with rogue until level 3. When you hit 3 you take the Swashbuckler Archetype.
Levels 4 and 5(and up)
This is when you start to take monk. In theory you don't need to take more than two monk levels. You don't need the monk archetypes and whatnot, but more monk levels is more movement speed, and mobility is the purpose of this build. And for that reason, I do suggest that at one of the levels when you get an ability score improvement that you instead use it on a feat. Specifically the mobility feat, which grants you another 10 movement speed. This would bring a 3 rogue/17 monk wood elf up to 70ft as their base movement speed.