Vagabond

Vagabond rogues are the unscrupulous scoundrels that can be found in countless realms. Operating outside the law, they bend the rules and distort the truth to get what they need. While they share plenty in common with other rogues, these outlaws have little use for tact or discretion, happy to engage in a tavern brawl or spontaneous duel, rarely patient enough to wait in stealth for the opportune time to engage. To survive in such a world, outlaws must become master swordsmen in toe-to-toe combat—and they can’t shy away from fighting dirty. If the blade fails to cut too deeply, the outlaw takes advantage of a swift shot from a hidden weapon, catching the enemy by surprise with a quick ranged blast.

Level 3: Roll the Dice

As a vagabond rogue, dice games and gambling come naturally to your dangerous lifestyle. You gain proficiency with dice sets. Whenever you roll initiative, roll 1d6 and add it to your roll. Then, you also get a benefit, depending on what you rolled:

1. You are immune to surprise this combat.

2. You can take skill checks as an item interaction this combat.

3. Your walking speed is 10 greater this combat.

4. The first cunning strike you use this combat is free.

5. You have advantage on your first attack this combat

6. You gain all benefits listed above

Level 3: Dirty Draw

You’ve learned that a fight is never fair, especially not your own. When you miss an attack roll with a melee weapon that would have triggered your sneak attack, you may use an item interaction to draw a hidden ranged weapon you can wield in one hand, making an attack with it against the creature. This attack does not have disadvantage if you are within reach of the creature, and can benifit from sneak attack, should it's conditions be met. You can make this attack even if you do not have a free hand, and after it is finished, the weapon is stowed away once again. 

Level 9: Flurry of Cuts

 You gain the following Cunning Strike option:

Flurry of Cuts (Cost: 1d6). When you deal your sneak attack damage with a melee weapon and then make an offhand attack on that same turn, your offhand weapon may also trigger sneak attack, assuming it meets it's other conditions (cannot be the same weapon changing hands). This cunning strike must be used on both the first and second sneak attacks you make as a part of it's effect. 

Level 13: Pirate's Port

When a creature you can see makes a melee weapon attack against you, you may use your reaction to add your proficiency bonus to your AC against that attack, potentially causing it to miss. Once per turn, if you use this feature on a creature and then deal sneak attack damage to it on your following turn, you may add an additional amount of die equal to your dexterity modifier. 

In addition, you have advantage on all checks related to operating or keeping stable ground upon vehicles you are proficient in driving, and those proficiencies become expertise. 

Level 17: Outlaw's Nature

When you use your roll the dice feature, roll 1d6 plus additional amount of d6 equal to your dexterity modifier. Each time you roll the same number twice, you gain one of the benefits below:

1. Reliable Skullduggery - Creatures of your choice that you can see cannot roll above a 10 for their initiative roll. (D20)

2. Sticky Fingers - Whenever you use your uncanny dodge feature, you may steal some of the power and momentum from the attack. During your next turn, add the amount of damage reduced to one of your sneak attacks inflicted upon that attacking creature, using the same type. (Flat Damage)

3. Swift Escape - When you take your cunning action, you can choose any amount of the options you have to choose between.

4. Cunning Blades - Once per turn, any cunning strike option you use with melee weapons add dice, instead of removing them. 

5. Unfair Advantage - When you have advantage on attacks with melee weapons, you may roll 3 dice, taking the highest result. If you roll more than one 20 this way, and the attack is a sneak attack, apply your sneak attack twice before delivering the critical hit bonus. 

6. You gain all benefits listed above