Apart from just fast traveling to all the holds and selling items to people for like 1k per trader, your best bet is to complete the thieves guild quest line. You are going for trophies anyway and that's one you will need.
Joining the Thieves’ Guild will give you access to a specialized fence, who you can sell stolen items to. Once you’re a member of the guild, simply go around the land stealing, raiding, and pickpocketing your way to success.
Merchants. Lisbet, a typical merchant. Merchants are specialized NPCs in Skyrim that buy and sell goods with you. There are different types of merchant, such as blacksmiths, apothecaries, or general goods, and each will only buy and sell certain types of goods, unless you have the Merchant perk.
You can sell items to a group of merchants until they run out of golds, save and close the game, re-open and reload the game, and resume selling items to the same merchants whose inventory and gold contents are reset.
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skyrim how to sell items
