[quote=Tuco]I also think there should be auto successes for pickpocketing, but that the difficulty gets higher the more times you try to pilfer from a single target in a row.
Something where it starts off rather easy and gives some validation to rogues and rogue-like characters, but gets harder the more chances you take so you can't abuse it too much without save scumming.
I like that idea. Maybe even just allow one successful attempt and then no more, because the trader (or whatever NPC) discovers he's been had, and is more careful now.
Or tie the number of attempts to the game's difficulty level. You only get one successful pickpocket on the same trader on Hard, Normal gives you a couple of times before the trader notices, and Easy gives you the current trader pickpocket cheese. It could also be done with adjusting dice rolls needed, but I like the "you only get a limited number of attempts on the same merchant" idea because it seems more realistic.