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leveling theivery increases the amount of stuff you can steal while sneaking. You can only steal once, from any particular vendor.
At the moment sneaking is useless unless you're using it for a stealth combat build, so just max theivery, if you come across hard to pick pocket enemies, just open dialogues with them and teleport them to somewhere where noone else is around.
Thievery skill determines the max amount you can steal. But as long as you're under the limit it always works.
That said you can get caught if the target moves and turns around or you don't flee the scene for a bit after stealing something.