I had a Diesel F350, I loved it, just got to where fuel was killing me, so traded it in for my Miata and bought a 97 chevy 1 ton gasser that sits unless I need a truck. I will say I loved my diesel when towing, it was a beast.
I've a friend selling his 97 Dodge Cummins, general consensus is that the auto tranny's are crap, they go out, the manuals are good. He upgraded his tranny with a custom built $5k tranny that just tows awesome, and he's got the power now. I like the Cummin's engines, the best on the market, their bodies seem to be cheaper the the other two, Ford has the best in that department IMO. Chevy's diesel's seem to be weaker and not long lasting, but they have the Alison automatic tranny's that rock.
If your going to tow with it, you will want a pyro gauge, I had a digital one that told me what my exhaust gases were, you will want one that can go in the exhaust manifold, not pre turbo. Will save your turbo from overheating. Also a boost gauge so you don't over boost. Diesels rock for towing, but are very expensive to maintain. My fuel filters were $30 a pair, air filter was $60, oil filters were $16, and took 15 qts of oil, and parts and labor charges are out of this world.
I did the math on daily driving my F350, maintenance, etc and getting my chevy gasser with a 454 was a better option. I don't get the milage a diesel does, but parts are cheap, maintenance is cheaper, and it more the makes up for not having the diesel.
Do lots of research, there are several dodge cummins boards out there, good luck in your hunt.