I wrote all this up, then I noticed that the feature was already implemented, but I didn't want this to be a complete waste :-/

Make Pick Pockets a selectable fighting style (perhaps in the same list as Berserk/Coward tactics, or as a toggle feature separate to those). Or perhaps, only have it usable if one hand is free - then it doesn't even need to be activated. When a PC lands a melee attack in Pick Pockets mode, eligible targets would have a chance of producing an item: "Your flashy fighting style momentarily distracts *foo*! Your nimble fingers swipe *item*.". This way, the amount of mind-numbing button mashing could be significantly reduced, but the Pavlovian conditioning of seeing rocks and tinderboxes appear from Pick Pockets is maintained ;-) Of course, this could encourage grinding as well, so some mechanics suggestions:

- when active, incurs combat penalties, mitigated by high Dexterity, Speed, being a Thief (Assassin too, maybe?), and perhaps other things like class powers, special talent(s), etc.
- chance varies depending on damage: higher % of target's max HP = better chance, criticals/stuns/other lucky hit effects might could also help
- only activates on damage portion that brings the target below its lowest previous HP value (so no waiting for monsters to heal, then damage to pick pockets again)

After all, as I understand, many methods of pickpocketing rely on distraction and misdirection, and what could be more distracting than an adventurer swinging her weapon at you?