I don't like pickpocketing but I have to reach 100 or my PC won't make it to level 81. Fair enough, that's how the universe works. I always reverse pickpocket my loot to the owner as I don't need anything and am just in it for the experience.

Having said this, I got tons of experience pickpocketing the sleeping members of the Bards College and the Blue Palace. Dragon's Reach was also good. I'll work my way through all the capitals but I don't think that'll get me to 100 (I'm currently at 62).

Any suggestions on alternative targets? FYI - it appears that you only get the experience the first time you pickpocket a target. Repeating the feat doesn't get you anything.

Also, I've see the exploits on YouTube but I don't wish to blatantly 'game the system'.

Thanks!