>>725592670 (OP)
Can work fine, but the risk vs reward of the action has to be properly balanced against the odds.
I'll use morrowind as an example, and no, not the combat. Lockpicking has no mini game in morrowind, you just use your lockpick on a lock and a dice roll weighted by your stats and the lock strength determines if you succeed. The penalty for losing the dice roll however is just that your lockpick durability goes down a bit and you waste a bit more time, so you're more likely to be caught by a patrolling guard (or you would be if morrowind had functional stealth).
Contrast that with pickpocketing in any post morrowind bethesda game (not counting morrowind itself because it's pickpocket chance formula is borked). Even when you have a like 90% very high chance of succeeding, the reward is massively outweighed by the penalty of being caught, because it immediately throws everything into disarray and you get chased by guards and maybe even the person you tried to rob. Pickpocketing should be a petty crime you do when you're starting off, but in actuality you usually want to wait until you're a master thief before attempting it much in these games.