I don't see picking pockets done anymore. There are two big and two little reasons for this, the two big reasons for this, in my experience, are: 1) Unless the player playing the thief gets a great magic item, they aren't interested., and 2) GM's don't like thier games sidetracked.
The two smaller reasons: 1) Everyone always has some change so the motivation to pick pocket a gem or coin is gone., and 2) Alot of the "goodly" GM's don't allow it, as strange as it might sound. As i remember one young GM stating proudly last year at a Con: They aren't thieves anymore, they are rogues. Only evil steals and i don't allow evil in my games. His rationale being that stealing was the same as taking food from an infants mouth, thereby depriving food from an infant somewhere in the gaming world
Back in the old days, gems and a few coins were always an awesome gain. Plus there was always the risk of being caught, which was great for a DM to take the story in another direction.
Yes, i separate the meanings of DM and GM, the latter being less flexible. I realize new-school players don't see a difference, but old-school players do.
The best thing i ever pick pocketed was a magical tome from a wizard. I also knew that being caught was surely death, but being a thief worth my weight, i successfully stole said item and made a pretty penny for it. Hey, it's what thieves do. We steal things.
One of the great experiences in gaming is when a thief tells the DM that he plans to steal something and the rest of the party's eyes bug out in silence waiting to see the possible consequences, if any, of said action. Good stuff! Thieves are the proverbial wildcards in DnD, for they can easily take the game in new and exciting directions. Too bad they aren't used as such much anymore. Gotta have a theif in a campaign, i always say.
BTW, i tell all my players that if you're playing a thief, i want you to use your skills for if you don't, i'm taking them from you. This motivates them to play in character and to do what it is thieves do when opportunity presents itself. A sidenote: if a character can't prove he used all his skills at a certain level, then when he levels, the skill unused doesn't advance. This way all skills-within reason, of course-are used by the thief and therefore be explained when he levels why he has become more proficient in listed skills. Obviously, if one is adventuring in the underdark (an example, only) and there are no pocked to be picked, then the rule wouldn't apply for leveling. I didn't really want to state the obvious but there is always one reader that misses the obvious. There are exceptions to evey rule, as they say.
Even though my thieves have successfully stolen coins, gems, and a magical tome, i was never so lucky to score a +3 ring of vampiric regeneration, a magical protection ring, or even a deck of many things. This, of course, doesn't deter them in the slightest, for there is always they great find out there for them that will change their lives for the better.
Great thread, DMMike