If you pickpocket a named NPC in Skyrim, stealing their gold and jewelry, will that NPC ever get new gold and jewelry for you to steal again?
Also, the same question for the same situation in Oblivion.
I'm confused about the issue. Personally I've never seen it happen in Skyrim as of yet. In Oblivion I never noticed a NPC regain inventory items/gold to be stolen again, except for one case: taking multiple Debaser swords from Agarmir in the Imperial City.