You should be able to get a V10 Ford in that price range and they generally have good reputations. Some Ford guy will know the good years vs problem years.
A old diesel may have a good engine but old is old. My 96 Powerstroke had clutch, starter, water pump, and other problems. All fixable but after a while it was one thing after another. The engine was solid, the rest of the truck was showing its age. It did have 250,000 plus miles on it so not shabby by any means. You could probably pick one up for $5000 and it will pull a TT just fine, but keep a couple of $1000 ready to fix things. It was easy to work on and did not require the latest electronic device to figure out what was wrong.
That said I love my Chevy but it is still a $20,000 truck after 8 yrs.
