Base Class: Rogue
You are comfortable in the midst of combat, preferring to stay up close and personal, and adept at using the din and clamor of battle to your advantage. Rogues who become Skirmishers are able to stride through a battlefield with equal caution and grace, and are able to take full advantage of the chaos of the situation to take out key targets on the front lines while sowing confusion among enemy ranks. Skirmishers' focus on martial skills are unique among Rogues, and they are valuable troops in battle, capable of decimating unprepared enemy forces.
Bonus Proficiencies
When you choose this archetype at 3rd level, you gain proficiency with martial weapons, medium armor, and shields.
Skirmisher's Guile
At 3rd level, your focus on melee combat improves your aptitude on the front lines. You may use your Sneak Attack against a target within 5 ft. with any one-handed melee weapon, even if it lacks the finesse property. Additionally, you may use your Sneak Attack on any creature as long as there is another creature within 5 ft. of it other than you, and you don't have disadvantage on the attack.
Shock Trooper's Momentum
You are now a powerful force in melee combat, able to create gaps in an enemy's lines by defeating key targets, and then use the confusion to stay alive long enough to do it again. Starting at 9th level, you can use the bonus action granted by your Cunning Action to grant yourself advantage on a melee attack against a target within 5 ft. of you, as long as there is another creature within 5 ft. of it, and as long as you didn't have disadvantage on the attack before. Additionally, if you reduce a creature to 0 HP with a melee weapon attack, you can take the dodge action as a free action immediately afterwards.
Combat Stealth
Starting at 13th level, your awareness of the blind spots in melee combat are sharp enough to allow you to attempt to hide, even while surrounded by enemies. If there are at least two hostile creatures within 5 ft. of you, you may attempt a Dexterity (Stealth) check to hide, lingering in the places that are seldom noticed within the clamor of battle. However, any creature that attempts a Wisdom (Perception) check to locate you after you have hidden yourself with this feature has advantage on the check.
Chaotic Warfare
At 17th level, your understanding of how to manipulate a battlefield in melee combat is unrivaled. You may now use the bonus action granted by your Cunning Action to force an enemy to attack wildly. Choose a creature within 5 ft. of you that is also within 5 ft. of another hostile creature and make a Charisma (Deception) check contested by the target's Wisdom (Insight). If you are successful, that creature must immediately spend it's reaction and make a melee weapon attack against another creature within 5 ft. of it of your choice.
Previous Versions
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Posted Nov 12, 2020So this class basically came out of the idea of using a rogue as a shock trooper. It fits pretty well with the natural kit of a rogue, and the concept of being able to sneak attack by using the chaos of large-scale melee combat makes sense. I thought that I could build the class to encourage you to build a strength-based rogue, since I find that build pretty cool anyway, and wanted a subclass that made it really shine. Being able to sneak attack with non-finesse one-handed weapons isn't actually much (if any) of a mechanical change, since all you're really doing is replacing a D8+DEX from a rapier with a D8+STR from a longsword, which makes exactly 0 non-flavor difference. Giving them medium armor and shield proficiencies makes it so you can make a tanky rogue, as long as you're willing to sacrifice a bit of stealth skills to get there, as wearing half-plate and a shield with at least 14 DEX nets you 19 AC. (If you want to power build, take medium armor master with at least 16 DEX; it cancels the stealth penalty and gets you up to 20 AC, which is amazing for a rogue.) I strongly considered giving them extra attack at some point, but that felt like it'd be a bit much, considering you can usually find a way to use your sneak attack every round with this build, since all you have to do is be surrounded by at least two enemies in melee, or go back to the old tried-and-true methods that all rogues get and get your party in there with you to proc it that way. This class should actually be a pretty interesting multi-class option as well, since it would let a character pick up the ability to do a 2D6 sneak attack when they take this class at 3rd level and use non-finesse weapons to do it, which would be pretty cool, and worth considering a dip for any sword-and-board characters as a way to pump out a bit more damage.