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Just a clarification on one of the above notes. They made a change in one of the patches so that you will always get the same results from pickpocket if you reload a save from before the attempt. Makes it much more difficult to up the skill, obviously. But yes, as someone else mentioned, if you can find an NPC that doesn't go hostile when you are caught and have a character with the charm spell, you can kill two birds with one stone. I believe Anne in Anrika is this way, with the added benefit that she 'lets you off the hook' when you sell her stuff that you took off her.
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