You can only pickpocket anyone once. If you try a second time you'll be caught immediately. So do a couple of tests and see what you can get. There is also a limit to how much you can take, I believe it's based on total gold value as I've been able to take anywhere from 2 to 6 things and that's after reloading and trying a few times to test it.
But pickpocketing is basically broke. You can take anywhere from 4 to 6 skill books from each one of them or a ring, amulet, etc. you'd like or some sort of combination. Or take his gold. The problem is you go and pickpocket every vendor and you basically never have to buy anything. Eventually your entire group has the best skills, the best gear and you're sitting on thousands of gold......
The only thing would be that as you level up and the vendors have new/better items you would have to buy them since you can't pickpocket them twice.
However you'll have lots of gold and as the game progresses you find new vendors
Last edited by Born2BWild; 23/09/17 03:49 PM.
