Training Pickpocket

 
Pickpocketing (version 1.0): 

Pickpocket NPC until it's out of stuff. If you're caught, reload. If he's out, go to another or sleep for 14 hours. (14, dunno why). I've used this and raised my 5 roguish types from pp of 8, three of them to 100 so far. High dexterity and speed seem to help increase this skill faster. - WithoutRemorse