So, I somehow wounded up with a lot of silver and gems. I made all of them into jewelry, and now have way too much. I keep trying to sell as much as I can, but the shopkeeper keeps running out of gold before I sell anywhere near what I have. --- The woods are lovely, dark and deep. But I have promises to keep
If you have the invest perk, give 500g to Lucan in Riverwood and he'll have 11,000. --- I need a woman like Jenassa. Spend a month away from home with a strange woman, come home to food, $2000 and sex, then leave.
Yeah. You'll need to do any combination of five of Delvin/Vex's quests in every major city aside from Riften, at which point Delvin will offer you a special job. Each special job done will upgrade the Ragged Flagon and your fences' gold reserve.
Two of them come from those odd jobs (Markath and Windhelm) there's also one in Winterhold, one in Solitude and one in Whiterun you get through the main guild questline (not sure if they ends up with 4k or not).
After doing all the odd jobs the Flagon itself has the fence with 4k and three other merchants, not sure what they end up with.