As far as I know:
1. Yes, no problem if your group was searched by the victim prior without success. You can even sell it back to the victim.
2. Very picky. If they find anything stolen from anybody during a search (not during bartering), you have to go to prison, fight or bribe. I'm not sure wether there is a persuasion possibility. I reload if such things happen.
2. I don't know exactly. No groblem at least after transferring stolen gold from your thief to the bartering char. I only steal gold (ok, I stole some skillbooks with lvl 4). With Thievery 8 I got 14,800 per steal, or so.
4. You can only pickpocket once per char and NPC, luckily.
5. Sounds great, if you like cheesy and unnecessary gameplay to get advantages. I have Thievery on one char and stole at lvl 4, 10 and 17 from some merchants. It works fine without overdoing stealing, if you have Lucky Charm (on Tactician).
Last edited by geala; 05/10/17 07:05 AM.