Heroic Outlaw

A Heroic Outlaw is a type of reformed Rogue, a thief, bandit, hitman or other who has decided to use their select skills to give aid to those in need. They may steal from only the wealthy and distribute the wealth among the common folk. They may incite riots to inspire political change. They may infiltrate and subvert the corrupt royal court. 
 Their almost superhuman feats of heroism and generosity inspire within them the ability to channel very precise forms of magic, in line with their ultimate goal to see the grotesquely powerful knocked down a few pegs.

Trained Fast Hands

Starting at 3rd Level, if you attack before an opponent in Combat, you can count your first attack against them as a Sneak Attack. You can also use the Bonus Action granted by your Cunning Action to make a Sleight of Hand check, use your Thieves’ Tools, or Use an Object.

Rustic Hospitality

Since you come from the common folk, you fit among them with ease. You can request minor aid from or seek shelter with the common folk of any location you visit. They will not risk their lives for you, and their willingness to aid is tied directly to their trust in you.

Beloved Rebel

At 9th Level, your infamy and skill have grown significantly. You gain Proficiency in 1 Ranged Weapon and 1 Martial Weapon, and Proficiency in the Performance skill. You also gain Advantage on Charisma Saving Throws, and Advantage on Deception checks against nobility.

Start a Riot

In a place you have been (now or previously) for at least 24 hours, you can attempt to incite a riot amongst the common folk. Make both a Persuasion and Performance check (DC 19), if both are successful, you may direct any common folk listening to you to riot in a direction of your choosing (ex. Toward the manor, East, down the Main Street, etc.) Once a direction is chosen, you cannot control or direct the riot further. The riot can last up to 12 hours.

Experienced Bandit

At 13th Level, your long history of acquiring valuables has increased your confidence in your success. You gain Advantage on all Sleight of Hand checks.

Robber’s Reward

At 17th Level Your heroic deeds, sense of justice, and selflessness have been rewarded by forces beyond your understanding. As if to coincide with your mission, you find yourself able to perform strange new abilities. You gain Proficiency in 1 Martial Weapon, and learn the Thaumaturgy cantrip, as well as one spell from the 1st Level Bard Spells list.

Balance the Scales

If you determine that you would like to steal from the rich to give to the poor, you can make both a Perception and Insight check (DC 19) to ascertain the location and amount of the resource most valuable to the corrupt individual in question. If your checks are both successful, you have Advantage on all ability checks and Attacks (if necessary) while you are attempting the theft. Whatever you steal, however, you must give away 90% or suffer Disadvantage on all Ability Checks and Attacks for 7 days.