Roguish Archetype: Scoundrel
These rogues traditionally use their dextrous abilities and fast hands for the oft-romanticised art of pistol duelling; though in low-tech settings, hand crossbows are also acceptable.
Though they lack the subtlety of others of roguish training, their skill with ranged weaponry and their swaggering confidence are a boon to any party.
Noble Art
When you choose this archetype at 3rd level, you gain proficiency in firearms. Once per turn, when you make an attack roll with a one-handed ranged weapon, you may add your Charisma modifier to the attack roll.
Quick on the Draw
At 3rd level, you may add your proficiency bonus to your initiative rolls.
In addition, when a creature you can see within the first range increment of your weapon takes an action, you may use your reaction to make one attack against it using a one-handed ranged weapon that you are holding.
Challenge of Honour
At 9th level, you may cast the compelled duel spell, at 1st level, at will with this feature. Charisma is your spellcasting ability for this spell.
While a creature is under the influence of your compelled duel, it qualifies for your Sneak Attack damage even if it meets none of the other requirements of that feature.
I Shot First
From 13th level, when you Sneak Attack a creature with a ranged attack, it has disadvantage on attack rolls against you until the start of your next turn.
Fan the Hammer
From 17th level, you ignore any Loading or Reload properties of your ranged weapons.
At the start of your turn, you may declare that you are going to Fan the Hammer, specifying a number between 2 and 5. When you take the Attack action that turn, you may make the specified number of attacks with a ranged weapon, instead of just once. Each attack you make with this feature suffers a penalty to the attack roll equal to 2 multiplied by the total number of attacks; for instance you could make two separate attacks with a -4 penalty each, or five attacks each with a -10 penalty.
To the Victor Goes the Spoils
At 17th level, when the object of your Challenge of Honour is reduced to 0 hit points, you gain temporary hit points equal to your rogue level + your Charisma modifier.