Thanks for everybody's feedback. I going to have to think about owning another diesel. The main reason I am looking is I want to get a enclosed race trailer so this would only be used on weekends.
I want to get an 97 or earlier truck since it less hassle to register. The Gen2 trucks seem easier and less expensive to work on. The 04 I had was not too bad just harder to diagnosis run ability problems. Never had anything major go wrong though.
From my research the main things that can get expensive is the lift pump failing which can take out the injection pump, trans is weak and a dowel pin that can fall out.