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And you might find or create potions. Ingredients with fortify pickpocket: Blue Dartwing, Nordic Barnacle, Orange Dartwing, Slaughterfish Egg.
EDIT: The enchantment is called Deft Hands. The Thieves' Guild Boots also have a fortify pickpocket enchantment.
Wow, rivers are full of pickpocketing boons.
The weight and value of the item you are trying to steal also influence your chances. Higher weight and higher value are more difficult. Gems/Jewelry are kind of a double edged sword. Their low weight makes them easier, but their higher values (especially on enchanted jewelry) makes it more difficult. The value of the item also influences XP gained. I think I've gotten 3 or 4 points with a single high value item.
The High Value ratio to Xp gain is new to me. Thanks. Argonian Poisoner, here I come!
If you want to increase pickpocket skill early on, the best way is to receive that hidden perk and then invest one perk into Pickpocket and combine that with any equpment you have.
Make sure that you have the Thief Stone and a sleeping bonus, then go on a pickpocket frenzy.
The quickest way to level pickpocket is to pickpocket enchanted jewelry. If you are lucky you will find 3-5 people in each city with something really valuable to pickpocket.
WOW! Did not know about that hidden perk, but it makes sense. I went to jail the first time ever and he said something different.