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Pickpocketing would make the most sense to me. I'd know more about which was the best way to shoplift if I did it more often, but I don't, because A) I almost always get caught when I try it, and B) All the good shops don't let you steal stuff anyway, and all the shops you CAN steal from don't have anything worth stealing. At MOST, you might get a Large Shield+1.
Having 100% in Pick Pockets might not be enough....I think I had Imoen that high, and she STILL got caught. It might be the total sum of all of the Thief's skills.
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Boots of Stealth: 1125 gp
Shadow Armor: 7875 gp
Slipping an Oil of Firey Burning down the back of Sarevok's armor: Priceless
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