Even if i'm undetected and make a successful roll for pickpocket the NPC somehow still knows I stole from them a few seconds later. Is it supposed to work like that or am I missing something?
I've noticed you can cheese it by promptly fast travel away after a successful pickpocket and just wait them out. But that doesnt feel right either.
Here’s the deal: Larian want to avoid stealing try and error and save scumming. Therefore they’ve added this DOS2 mechanisms where the NPC will check if their belongings are still there. This mechanic is just silly and the fact that you can steal a merchant is even more silly.
Sleight of hand should be used in missions and so on, not to become a rich person.
BG2 added a mechanism in some of the main merchants that they cannot be robbed. That helps to sustain the game economy. There’s only a few merchants that can be stolen and even so you could be spending your money to buy that goods because the amount of gold gained through quests was enough to purchase everything you possibly wanted.
Going that path is again going for the divinityzation.