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You gotta use another party member to pickpocket that same person or else you’ll never get another chance
Note that the limit is per character, so you can just respec thievery on someone else and steal again. This includes the hireable mercenaries.
With the right gear, you can boost it upwards of 8 points to steal tons of gold off vendors.
Money eventually becomes meaningless, though, so it’s nothing more than something pretty to stare at in your inventory... I ended up having like 8+ stacks of 99,999 gold... it’s ridiculous
but what about letting u pickpocket again after like an in game week or something?
I get why immersion wise it sounds stupid to not steal again from the same person, but game balance wise, it's needed, but still easily able to be worked around. As others have said, you can respec other characters to thievery, and early game you can dismiss them and recruit someone new as a shadowblade, get all skilled up for another civil point, and steal with 2-5 extra characters there.