I think that if pickpocketing is allowed on a server, people shouldn't be surprised to get their pockets picked. It's part of the game there.
And as long as your attempts are either succesful or failures, but you remain undetected, noone should complain. That is to say, as long as it only happens now and then. If you go out and completely empty every backpack and take each purse you come across, then of course you are overdoing it and deserve a good smack on the head [img]smile.gif[/img]
The main idea is for everyone to have fun. You'll have to make a few compromises, but on the whole playing should be an enjoyable experience. Two or three pickpocket attempts on a person should be fine and noone should feel upset by it. Although I do feel you shouldn't PP from players rated effortless or easy, as they can't do anything themselves even if they catch you, or those rater impossible, as you don't want to be caught by them but also because it is s overy annoying to them to be robbed blind by a little pipsqueek such as yourself [img]tongue.gif[/img]
In character, if everyone else seems to have tons of money and you have very little, I can see how it would be 'fair' to redistribute a little here and there. You should keep in mind that pickpocketing is considered an offence in almost every society you find in NWN games, and that if you are caught you are in for some trouble. Running away succesfully might still mean you have to avoid certain people, and they might spread the word. It could turn out very badly for your character. Because of that, there are really only two ways to pickpocket.
One is to lure people to an area where they can't really run away, ask OOC permission to rob the victim, roleplay some threats and empty the victim's pockets good (or just ask them to hand over some coin). Yes, there are serious consequences involved here, but there's also a lot of coin to be had.
The other is taking the oppertunist's approach. In game, that's making one or two pickpocket attempts at a random victim where it is crowded. If you are succesful, after all, who will know it was you? And if you are caught, you can easily get away without drawing too much attention from the other bystanders.
In the case of a TN alignment, intentionally robbing people to get some coin is not a very usual course of action. Taking small amounts from random victims would almost certainly be better. However, you only pick pockets if there's no better alternative at earning money.
If you are not 'out to nail anyone', then you shouldn't really be picking pockets. In fact, your character should hardly be interested in spending points on the pickpocket skill. Why would you spend time learning something you never wish to use? And the best thing is; you'll have more points to spend on other skills so it won't be one big waste of points after all