So baisically you just sell him [censored] until his moneys gone?
Yup, I tend to have a lot of high quality jewels and jewelry stored up over the past few adventures, most of which are worth enough to make decent return after selling a few. On average, I've seen Merchants have between 700-2000 gold on them at any one time, and this is without the Speech perks. Most of the trinkets and gems I find have a base value of around 400-800 a piece.