I had a 97 1500 4x4 slt with the 340 engine. I sold it 3 years ago for 2 grand. It had about 170k miles on it. It was a great truck, never had transmission issues. When I towed, I disabled the overdrive...
oh ya, it was that lovely sh$t brown color...
Thing was that I was only offered $600 for trade in, and there were tons of used trucks on the market here. I put it on ebay and a guy from maine purchased it. He said there were not many trucks for sale up there.
Maybe extend your search area and save some money by buying something further away where there are more trucks up for sale.