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1. Head to The Full Coinpurse and sell all the loot from the prison escape. Object: Gold 2. Go to Aleswell and complete the quest. Object: Bed and storage 3. Chorrol and start Separated at Birth. Object: Honorblade of Chorrol (eventually) 4. Deliver the Amulet and grab some armor. Object: further main quest, more money 5. Bruma find and complete Two Sides of the Coin: Object: A set of chainmail armor and Silver Longsword plus the stolen loot. 6. Chorrol complete Separated at Birth the waste time until Fathis Ulis shows up to tell me where to find an unidentified object (Honorblade of Chorrol). Now I have some gold, a decent set of armor, a really good zero weight weapon, a place to sleep, and a storage trunk.

Not to mention getting the best set of light armor in the game.