[Ivramire]

It was a little difficult at first when the skill level is low but if you put one or two perk points into the +success chance you'll be able to take most small items easily. Taking gold, keys and small items builds skill so quickly that you won't really fail after a certain point. You can even get multiple skill-points stealing from just one person.


Edit: man, having a high pickpocket skill is so corrupting. Just started a quest where someone asked me to talk someone else into forgiving them the debt they owe. The quest-giver is out on his luck so can't pay the debtor. I pickpocket his last two gold anyway.