The problem right now with pickpocketing as I see it is, well is that is the RP just doesn't support it. There can be no lead up, no chase, no pose to react off of. The effort the pick pocket would put in is far less than the effort I or another player would have to put in to start a scene to spot them... Is it even possible to report thieves to security, assuming that it's a place with security characters 24/7?
Beyond those issues, Pickpocketing IRL is like street magic, the people who are good at it, don't just grab your wallet, and run, that's a suckers game, they engage a target, steal the cash, and leave the target unsuspecting that anything happened. It uses a lot of techniques that are social manipulation, sleight of hand, and distraction. Not just blunt dexterity... Because even in a busy bar, personal space is still pretty easy to maintain, especially when seated at a table or a booth. A quick hit, or purse snatch as it's usually called, relies on a target being in the streets. A personal preference of mine would be that this be RP'd out, because Sindomes model seems to encourage everything else being a function of RP, but pickpocketing seems to be the one place where people seem to turn a blind eye to pure mechanical play...
Want to read up on how to RP pick pocketing, look up a book called "Techniques of the Professional Pickpocket" by Wayne B Yeager, the second result on my google was a full PDF, the actual 70 or so page document is expensive as fuck to find a copy of. But it gives a very brief rundown of common pick pocketing techniques. Get flavorful with your RP, get into character, don't just, "I pickpocket the man," Roleplay it, and if they aren't perceptive enough to notice the switch, they shouldn't RP that they do... I'm basically asking for pickpockets not to be sanctioned meta here. Because that irritates me in my very black and white heart. If you want to be covert you should have to be so in character.
As an aside having never Pickpocketed in game, I'm not sure if some of this next bit is actually possible.
I would love to see much harder pick pocket checks to steal Phones, Wallets, and watches, even if the watches are being worn.
I would love to see random NPC snatchers and pickpockets wandering the streets and bars that are easier to foil than the average PC. So that we don't know for absolute certain when we get pick pocketed it was probably a player. At times while the atmosphere is great in the writing, I don't feel much fear in Red Central OOCly, because I know the only people likely to harm me are players, and they are easier to notice.
That's about all I've got. Hopefully a bit more respectfully presented than before, as I did get pretty tilted in that thread.