To be honest, I've never played the compulsive pickpocket. Smuggler, sure, but never quite compulsive pickpocket. Nor have I ever killed her and looted her corpse. I should do that.
I do remember playing through with a Gifted character and heavy drug user. Managed to go through the qualifying test for Vault citizenship high as a kite and pass with flying colors. Also was a porn star.
I took out the whole of Vault City with a Bozar. There's something about the overkill/critical hit animation, which blows the target's head and limbs off, that's very, um, satisfying.