A friend of mine showed me a way of pickpocketing the SAME mob up to 7 times. Now it's been some time since I played a rogue, but the trick is to keep strafing around them while spamming your pickpocket button (keybind works best) and JUST be out of range to pickpocket.
A bug causes you to pickpocket up till 7 times. @ lvl 70 it can be good cash.