I recently purchased a 1998 Dodge 2500 (2wd) with the cummins diesel and a standard transmission. It is meant to pull my 12,000 lb flatdeck trailer. They are a very good combination. Always buy one step bigger than you expect to need, because sooner or later a ferret or a carrier end up on the trailer.
Downside to the Dodge Diesel is the the poor starting in the winter months. The truck has to remain plugged in overnight at -25 to be dependable.
The decision to buy a 2 wheel drive was possibly a mistake, but I primarily wanted the truck for highway towing. The rear diff is a positrak (standard on the cummins equipped trucks) so the truck isn't bad, but if I were to end up in a ditch during the winter, I would not expect this truck to get itself out. The 2 wheel drive option also gives a higher towing rating.
The reason for an older truck was simply economics. Price was only about 8K, and insurance is especially cheap (under $600 a year). Also, I believe the older Dodges get better mileage than the newer stuff.
I towed a couple of GMC 135 deuces home last fall, and the truck acted like nothing was even attached.
Good luck on your hunt for transportation.
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