I have never owned a diesel anything. That said, if I could find a 1st gen with a solid body I'd love to have one. That said though, my son has a 92 W250 club cab,with a problem that we so far cannot figure out.
Truck has 140K original miles. 47RH ("618") trans. He bought it with 123K miles and all service records since new, has had it about a year and 1/2.
This is 2nd winter he has owned it, and has not driven it except on the nicer, warmer, salt and snow free days in either winter, he has another (gas) truck he saves for driving in snow and salt.

Just over a year ago, he broke the flexplate. We pulled the trans and replaced it, and although the PO had claimed to have had the trans done, he had it done again "while it was out" by CRT. (they are not that far from where we live, about 40 miles) 5K miles later, blew another flexplate, this was a "Pioneer" brand from parts store.
We have had a tough time finding the "right" one as this is non lockup trans and everything we see says the '94+ flexplate works and most current parts listings call for this now. Took it to a local diesel place where they did it again, this time found a cracked engine to trans adapter, which was replaced/ and he went with an SFI rated aftermarket one. 5K miles it's making the same noise again as it did the previous 2 times just before I had to go after him with a tow strap. 98% used as daily driver, what he has towed with it are loads I would barely be leery of pulling with my 1st gen Dakotas. He has a higher SFI rated flexplate here, like 2x original thickness. He loves the truck but is getting tired of this recurring issue. We both know of Cummins owners that have been running them for years and years with a whole lot more abuse and never having had this problem. He is starting to search around for the parts to convert to a stick, something that he has considered since the day he bought the truck, even before the 1st problem ever surfaced.