I dunno if it's just a quirk, but whenever I try to steal from a vendor, I have the person with the highest Charisma talk to them, then I sell a few things, buy a few things, and THEN try to steal something. I keep a few jewels around so that I can sell them when I want to steal something.
I dunno if this is a viable strategy, but it's worked for me in the past. Remember to save after you steal... every time! I hate going through the dialogue to get to steal somethng I've already stolen twice...
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