![]() Therefore, light but expensive things provide the best balance of skill gain to risk. Keep in mind that skill gains are based on the value of the item, whereas the difficulty is a combination of weight and value. If they're following you, though, you can always take the money back out of their inventory if you get stuck in this situation. The only downsides to this is that you can only train 5 times per level, and that it's relatively easy to end up with the trainer carrying too much gold for you to feasibly pickpocket. Some skill trainers are also followers (the Companions come to mind immediately), so you can do a little of both if you so desire. If you try to take an item, and your target suddenly turns around, it means you’ve been detected. Pay them to rank up a skill, and then pickpocket the gold back. If you pickpocket fairly often, it’s inevitable that you will be caught. You can also level this easily with skill trainers, as money paid to them for skill training ends up in their inventory. When Astrid kidnaps you and you awake at the Abandoned Shack, the three hooded hostages are ideal pickpocket targets: they will never report you even when caught, they have very low perception and are easy to. alchemy, enchanting, pickpocket, sneak and other skills, and craft the best. The best way to level pickpocket without save scumming, bar none, is during the quest 'With Friends Like These'. If you fail, I think you have to wait 2 days before you can steal again, which means that quicksaving/loading is probably faster. There are only a few Enchanting trainers in Skyrim, but the easiest trainer. (Lydia tended to just say something to the effect of "I saw you, but I'll let it go. ![]() In my experience, if I failed I didn't get a bounty, but your mileage may vary. Ask her to take something expensive, but light weight (ie, a ring or necklace). I found this pretty easy to do with a follower, such as Lydia.
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