a soft implementation of failstates could be the best : not that hard to program (still eating up ressources though) : you could allow a few misses before punishing the player, or each time decrease player reputation. the same problem arises with synergy between skills (fast-talking your way out of failure, creating a distraction, etc) to avoid hard failstate and thus constant reloading

soft skill requirements : those are an open invitation to savescum, but you could introduce new variables (target is sleeping, alone/in a group, trusts/mistrusts you, etc), although pickpocketing being way too minor an aspect in most of RPGs, it's only natural no programer will ever put the time to do that hard skill requirements Г la Arcanum that eliminate reloading but also feel gamey Sure, some exist or could exist but they're far from ideal (excluding systems Г la Thief, that depend on player skill) : If you get caught, it's the same as stamping on an infant and the entire town will try to murder you on the spot, even if they're in their house all the way across the map when it happens.Д¬lick to expand.A gamist approache can feel weird, but unfortunately I don't see a perfect solution on the simulationist side of things either. Let's be real, though: This is far too much effort for the average development team to even approach implementing. It might also feasible that if your character pickpockets someone and gets caught, but is able to run away and hide quickly/effectively enough, you escape immediate consequences but gain a little bit of 'infamy,' increasing the odds (note I say 'odds' I don't mean a straightforward reputation system wherein everyone in town automatically knows that you're a -5 Scumbag) that people will recognize you as a troublemaker when you're trying to get up to no good, meaning that eventually a town or city become too hot to operate in safely. With crowds, it would be feasible to simulate failing but not being identified, or being tentatively identified but vanishing into the crowd before anyone can really do much of anything. Due to CPU, GPU, engine, and/or design limitations (money), you get about twelve people in each town.

As I see it, a major issue with pickpocketing is that RPGs tend to lack crowds of any sort: a crowded theater, busy city streets, etc.

Divinity original sin 2 pickpocket mod