Charming Scoundrel

From birth, you have been interacting and surviving in urban territories, learning from your surroundings. Charming Scoundrels are as charismatic as they are unpredictable, they are adept at lying and persuasion as a means of getting what they want, and go through questionable means to achieve their goals, often using other people as their leverage.

These Scoundrels are both loved and hated by the societies they live in, they can be the people's face, using their charm and sharp tongue to give them a better life, or they can be filthy smugglers, being oftenly confronted by the authorities, only to be let loose again because of the rumors at the tip of their tongues, and the money on the palm of their hands. Charming Scoundrels are known by the people, and they know even more about those people.

Deceitful Artist

You are highly skilled in tricking other to gain the upper hand.

When you reach 3rd Level, you learn the Minor Illusion Cantrip, and you have advantage in any Charisma (Deception) Checks made to make other believe the illusion made from that spell are real.

Additionally, you learn to make use of your wits in the middle of combat. As a Bonus Action, you can unsettle a creature you can see by taunting or telling a lie that would affect them, make a Charisma (Deception) Check contested by their Wisdom (Insight) Check, if you succeed, you can use your Sneak Attack against them even if you don't have advantage on your attack roll. When you roll your Sneak Attack damage this way, you can treat all 1s rolled as if they were a 2. At 9th Level, you can treat all rolls of 2 or lower as a 3, At 15th Level, you can treat all rolls of 3 of lower as a 4.

You can use this feature a number of time equal to a third of your Rogue level and you regain all uses of it at the end of a short or long rest.

Master of All Trades

Throughout your life, you have become adept in many different talents to aid you.

At 3rd Level onwards, you can add half your proficiency bonus, rounded down, to any ability check you make that doesn't already include your proficiency bonus.

Additionally, you can choose 2 skills, you become proficient with those skills, alternatively, you can choose to gain proficiency for a new language or tool instead of a skill.

Dirty Fighting

By 9th Level, you have learned to change the odds of an encounter to your side through your own means.

As an action, you may attempt to blind a creature within 10 feet of you by covering their eyes. If possible, you can use an object that could obscure a creature's vision, such as a handful of sand or the glimmer of a coin aimed at their eyes. The creature must make a Dexterity Saving Throw, on a failure, they are Blinded until the start of their next turn, on a success, they dodge your attack and aren't Blinded. If the creature is hit by this feature before rolling Initiative, they are also Surprised until the start of their next turn.

The Saving Throw DC for this feature is 8 + Your Proficiency Bonus + Your Dexterity Modifier

Famous Persona

At 13th level, you know how people are prone to act and react to each other's demeanor. You gain advantage in all Charisma Checks and effects that can cause charms made towards a creature that is not directly hostile towards you, provided you share a language with it.

When a creature that shares a language with you becomes hostile towards you, you can make a Charisma (Persuasion) check contested by the creature's Wisdom (Insight) check, if you succeed, the creature and all it's allies, if any, are charmed by you and 5 other creatures of you choice for 1 hour. If the creature is missing any hit points, it automatically surpasses your check to charm it, if any of the charmers deal damage to the charmed creatures, the charm ends on all targets and they become immune to this effect for 24 hours.

You may use this feature twice and you regain the expended uses once you finish a long rest.

Brothers and Sisters!

 At 17th Level, your influence through people is undeniably powerful, you have learned how to make them listen, and how to make them shout.

 You can attempt to persuade a crowd into taking action. You Learn the Mass Suggestion spell, and can cast if without material components. If you spend 10 minutes making a speech, there is no limit to how many creature it affects

 The Saving Throw DC is 8 + Your Proficiency Bonus + Your Charisma Modifier

 Once you used this feature, you can't use it again for 7 days, and the previous targets of this feature become immune to it for 1 month.