When it comes to diesels, it is not the motor that I would be worried about. Most diesels will go for 300K miles before needing a rebuild. Yes there are those stories where people go a million miles but those are few and far between. My little Mitsubishi diesel is a very reliable truck but the motor has been rebuilt twice and it has 290K miles on it but the body has held up great. My little Mitsubishi has a shorter lifespan than these newer diesels because it is not intercooler, roller rocker head, it did not have a watercooled turbo etc. Since Mitsubishi has taken steps to cool the engine it has become much more reliable and the life span has improved greatly. These little motors went from lasting 100K miles to last 300-400K miles.
With the exception of the Powerstoke 6.0 (I have just heard to many horror stories, but with the proper upgrades they can be very reliable) all diesel over the last 20 years are great motors. Even the GM 6.5 was a decent engine. Was it as reliable as Cummins? No, but it was still a good engine. The biggest concern I would have would be the rest of the vehicle. How well has the body and interior held up. Most of the older Dodges I have looked at, the doors do not shut properly, the interiors are falling apart and rust is taking over. This is also the case with GM and Ford.
Most diesels are a working mans truck and they get worked. I would look for one that has lived an easy life. Look for one with out a fifth wheel hitch, with out power mods, a big lift, and a beat up bed. These are the trucks that will last the longest.