You can only rob an npc once and that's it, you can never rob them again.

Stealing items and gold is a great way to save (and make) some cash without breaking the bank, just keep what I said in mind about picking your targets. Also sometimes if someone else takes an item from a completely unrelated npc and they search you, they may get miffed by you simply having stolen goods even if it's not theirs so bear that in mind when sending items with the stolen tag to your team mates, while you may have run out of range of the search a team member may get the shakedown in your place. Yep, the stolen items becomes an issue if the person you stole from stops and checks you, but that is pretty easy to evade like I said if you simply walk a good distance away from them and wait a minute or two after you rob them blind. If I can help it, I tend to wait to do my stealing when I know I am close to the end of that act and won't be returning to that area anymore anyway. I try to space my thefts out since gaining a level or two will see the vendors get different items that you may want more than the last ones you stole and then you're out of luck. I currently have rank 9 in thievery (5 base, 1 thievery dagger, gloves, belt, chestpiece) at level 17 just about to leave reaper's coast and most vendors don't have much worth taking so I just nick their gold, usually 22k+ each from most of the vendors. Keep in mind that some weapons and armor are pretty heavy which will push you to your weight limit quickly, and in those cases it often behooves you to simply take the gold instead depending on how much the vendor has at the time, you'll get a feel for it after a while. It will give you plenty of time and indication on if you are approaching your steal limit. If they have several choice items then I will steal as many of them as I can and then fill out the rest of my theft with gold, this is most easily achieved if you make one of your party members speak to the npc while you casually browse what it is you want to take. I digress, for me personally, it depends on what the vendor has. The stolen tag is pretty meaningless, you can rob an npc, and then immediately run out of their range for a few minutes (until their 'search' passes) and then walk back up to them and sell their crap back to them if you wish heh.

Divinity original sin 2 gold