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If you go the way Greystoke suggested, I'd recommend stealing from the Innkeeper to start off with. He's by far the easiest one (take a look at the surroundings, how could he keep track of ANYTHING?). Later, build yourself up to stealing from Arms of Argus, Belcanzor's, and Paluke's (when you've got the skill way up). Make sure you don't make an enemy of Paluke, though, as he's got the best prices for you to sell your found goods as well. I traded with him all the way through to the endgame.
-Sazerac
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