I try to play the thief stealing according to the alignment of the party leader. If the leader is Lawful Good I don't feel they would appreciate one of their party constantly ripping off vendors. In most other cases I feel free to steal. Also, I don't see a problem with selling and reselling. I imagine the theif tactic not as a pickpocket of the item and then trying to sell the item back. I look at it more as the theif getting the vendor to give back the incorrect amount of change. We've all heard the old line, "I gave you a $20 not a $10." I know the game doesn't portray it that way, but I guess that's how I explain it.
Possible spoiler . . .
Don't max out your thieving skills (280 pickpocket) by drinking something like 5 potions of mater thievery. I've gotten caught. To steal efficiently keep the percentage around 230 and you should be fine. I always try to get the right percentage and try stealing from some thief that is expendable (like the fencer in Gaylen's home -- upstairs) so that if she gets angry I can wax her, drink another potion and head over to the Copper Coronet.
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