Seems to me that scripted events in which you get pickpocketed if carrying a lot of money would be nice.
Actually now you say that I had a weird event in riften, i'm with the thieves guild and when in the market one time i heard a scuffle behind me, turned round and a dead thief (cant remember exact title) lay just behind me, and my followers were standing closer than normal alongside some guards...so i took the dead thiefs gear and sold it at the market


