Base Class: Rogue
Any Rogue that pursues the life of a Bandit knows that even if they have to put themselves first, it's with friends and allies that they will thrive. Capitalizing on their underworld contacts particular skill set a Bandit can deftly weave through any fight or business deal and apply their own particular brand of brute efficiency to get the job done.
Not averse to using surprise and deceit to get their way, any successful Bandit will have you looking one way while in the other they're getting what they want, be it taking the money from your pocket or putting a knife in your back.
Harsh living
Starting at 3rd level, you gain proficiency in the Intimidation and Survival skills if you don't already have it. Your proficiency bonus is doubled for any ability check you make that uses either of those proficiencies.
Savage Ambusher
Starting at 3rd level, you are no stranger to getting the drop on your opponent, knowing that landing the first blow can be the difference between victory and defeat. For the first round of combat, after rolling for initiative, your walking speed increases by 10 feet. If you have a climbing or swimming speed, this increase applies to that speed as well.
In addition, your first attack roll of the combat has advantage if the target has yet to act yet in that combat round.
Practiced Plunderer
As of 9th level, you've become accustomed to quickly rifling through others belongings and finding hidden compartments. As an action you can gain advantage on all ability checks using Investigation and Sleight of Hand for 10 minutes. You can use this feature a number of times equal to your Wisdom modifier (minimum of once), and you regain all expended uses of it when you finish a long rest.
In addition, if you spend at least 1 minute observing or interacting with another creature outside combat, you can learn the approximate value in Gp of their property and belongings that you are reasonably aware of.
Exploit Opening
Starting at 13th level, you've become accustomed to taking advantage of distracted opponents as they battle your allies. When an ally fails an attack roll against an enemy that is either adjacent to you, or you are hidden from, you may use your reaction to immediately make an attack against that enemy with advantage. This attack can benefit from your Sneak Attack.
Perfect Raider
At 17th level, you have learnt how to slip past your opponents defences, focusing on those who are already weakened. At the start of your turn in combat, if you are not Incapacitated, Prone or Restrained, you may move 5 feet. This movement doesn't provoke attacks of opportunity. In addition when you make a weapon attack against a target who has less than full Hp you score a critical hit on a roll of 19 or 20.
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