Purely a roleplay aid, but it would be cool if a rogue who's successfully pickpocketed someone could also add in a little calling card, as if to say "Yes, hello, I was here." Also offers something a little more for the victim instead of just a message that they lost 10-20g. Just something to consider.
Quietly reverse pickpocket poisoned health potions into potion sellers inventories.
Putpocket enthrallment items on a person's inventory.
Subtlety putpocket gold to a beggar without him noticing and asking if you have any more.