1. Find npc who trains you in a skill 2. Save game 3. Train with them 4. Pickpocket your gold back from them 5. Repeat
Your pickpocket skill and trained skill will go up really fast and your levels will too. Keep getting the pickpocket perk that increases likelihood that you can steal something. Once you cant train anymore, you can go around in towns stealing everyone's valuable items.
If you fail, reload the save.
Also, its so much fun once you have skill 100 to go around stealing people's clothes that they're wearing. --- Movies watched in 2011: 133 Xbox Live Gamertag: The Koopa Bros
Where can I find a trainer for pickpocketing? I curious to know because I haven't seen a trainer in that yet. --- "Hey, I calls 'em like I sees 'em." http://28.media.tumblr.com/tumblr_ljf891lTwu1qh77rwo1_400.jpg