I've been using a 1995 F-250 super cab 4x4 with a 351 engine to pull my 10,000 lb. boat over the last couple of years. The engine in the truck is acting up so I thought I would do a little looking around before I dumped any more money in the truck.
Wow! The price of diesel has killed the resale value of diesel trucks. I wound up buying a 2wd 2006 Ford F-250 XLT Crew Cab Powerstroke with 32K miles for $15K. The truck could use new tires but that's it. This truck sold for $40K when new. What's even better is the truck is under full factory warranty until October (or 36K miles) and the engine is covered by Ford for 5 years/100K miles. The only real flaw is a dent in the bottom of the bed behind the driver's wheel (visible in the picture).
I know the price of diesel is high but it's hard to pass on a truck at this price with the towing capacity it brings to the party!