When can I go on another pickpocketing spree?

Having picked just … all the pockets, the towns of Skyrim are now well dry, so no more gems and rings and amulets for me.
But it stands to reason that these respawn, so when and how should I expect that to happen, if at all?
Moreover, if and when they do respawn, are townspeople's pockets affected by Prowler's Profit? (The Barenziah bonus)
Best Answer
As far as I can determine, for named NPCs; their inventory does not respawn (additional source).
So if you pickpocket, say, Jarl Balgruuf; his inventory is static from when he is first loaded, and anything you pickpocket off him will never return. (Insert region here) Guards, however, are not necessarily static, and may have their inventories reset with the rest of the map cell they reside in if it has not been visited in 10 in-game days.
There may be some odd exception cases; particularly if a specific NPC is called upon by certain quests, it may generate a fresh version of that NPC complete with fresh inventory.
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Can you be pickpocketed Skyrim?
Pickpocket is a skill in Skyrim and is one of the six skills that fall under The Thief play-style. The intent of the Pickpocket skill is to provide greater role-play opportunities and much more realistic thievery. The Dragonborn is free to peruse their target's inventory, without breaking the law.Do NPC inventories Respawn in Skyrim?
Named NPCs respawn if you take everything. Generic NPCs do or don't respawn, if you do or don't leave an item on them. Specific followers/named NPCs/generic NPCs respawn items according to hidden rules that Bethesda made up that no one can figure out.How do you get a pickpocket to 100?
Skyrim \u2013 How to Pickpocket Successfully5 TIPS YOU NEED to AVOID PARIS PICKPOCKETS
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