
Dox of the ParaDox twins |

Hello friends. I am going to be playing an Obitu bootlegger in an upcoming campaign and I'm stumped at what class or build he should be. I have the role play and character figured out pretty well. But I have too many ideas for what he could be.
I was thinking maybe a Brawler, Investigator, UnRogue, or Vivisectionist. But I'm open to other ideas as well. Thanks all.

avr |

The sly type - that's not a brawler at least. Given the obitu cha penalty, a smart character with the clever wordplay trait might be your choice, and that would work best as an investigator or vivisectionist given the ability requirements of those classes.
From there a vivisectionist is better at stabbing people as part of a gang (which is the default use of sneak attack if you look at the rules, it's less about a backstab) and using wands, and an investigator is better at skills including that talking their way out of trouble.

avr |

A vivisectionist isn't as dependent on sneak attack as a rogue but they do get just as much of it and setting up an extra way to achieve sneak attack is worth doing. On the other hand they don't really need TWF since they're likely to be using natural weapons, either from feral mutagen or a polymorph extract. Without bombs they probably won't need extra discovery, the discoveries built into the class will do.
Some ways of getting sneak attack more easily: dirty trick combat maneuvers (to do in the same round 3+ feats, BAB +6), press to the wall (2 feats, BAB +3, ideally with flight), feints (not recommended), circling mongoose (4 feats, BAB +6), shatter defences (3+ feats, BAB +6), gang up (2 feats, needs a couple of melee allies), and basically anything else which blinds the enemy.
Spontaneous healing is a good discovery and you probably want feral mutagen. Glimmering infusion lets you effectively cast glitterdust spontaneously (which is another way of getting your sneak attack working). Wings, infusion, pheromones and other mutagen discoveries are worth looking at.

Skrayper |
The most "smoothtalkiest" class I've seen is Negotiator Bard. Plus it gets rogue tricks in place of versatile performance, so that lines up well - plus the additional skill points means he can flavor out a bit more there.
That said, you won't be nearly as effective in combat as the posts already up.

Dox of the ParaDox twins |

A vivisectionist isn't as dependent on sneak attack as a rogue but they do get just as much of it and setting up an extra way to achieve sneak attack is worth doing. On the other hand they don't really need TWF since they're likely to be using natural weapons, either from feral mutagen or a polymorph extract. Without bombs they probably won't need extra discovery, the discoveries built into the class will do.
Some ways of getting sneak attack more easily: dirty trick combat maneuvers (to do in the same round 3+ feats, BAB +6), press to the wall (2 feats, BAB +3, ideally with flight), feints (not recommended), circling mongoose (4 feats, BAB +6), shatter defences (3+ feats, BAB +6), gang up (2 feats, needs a couple of melee allies), and basically anything else which blinds the enemy.
Spontaneous healing is a good discovery and you probably want feral mutagen. Glimmering infusion lets you effectively cast glitterdust spontaneously (which is another way of getting your sneak attack working). Wings, infusion, pheromones and other mutagen discoveries are worth looking at.
Thanks for the great advice. I appreciate it