Quote Originally Posted by BRKNdevil View Post
Barbarian because it gives you the Unarmored Defense, Fighter for the combination of fighting style, and Battlemaster for the alternative attack Flair, and cunning action only gets you the hide option, whose use can be easily negated depending on the situation and suits ranged characters more then melee. What you described wasn't a swashbuckler but the poorly trained throwaway character from an old pirate movie. A swashbuckler seems to have always been a lightly armored upfront and skilled fighter that seems to have originated in the period when a fencing sword was civilian legal. the Weapon choices prevent you from doing some of the more traditional fencing styles such as pairing a rapier and a dagger and if you decide to mention the use of the feat Two Weapon fighting. Then the use of such a pair becomes extremely subpar. Basically going rogue is fighting without flair and being a sneaky git as well, which doesn't really fit the image of a swashbuckler. In comparison to 3.5 character classes, your idea wouldn't fit there either.
1. Actually Cunning Action allows the choice between Dash, Disengage, or Hide as a bonus action. Also, the rogue can be every bit of a quirky, snide character as this could as it just requires that he has advantage on the roll or if he "flanking". The question really is how.
2. While I have to disagree on the Barbarian comment from AgentPaper you still are doing a lot of splicing and I would also agree that why is he Macguyver. I do like that you relegated some of the other things as deeds but the dares still trouble me. I mean when you look at the Pathfinder Gunslinger remember how much grit he could have at one time? Like a little more than their wisdom modifier worth, here though you are still giving them a Monk ki pool with all sorts of additional regenerations.