I had a 95 6.5TD and loved/hated it. Great mileage comparable to my first gen Cummins and really good power once you upgrade to an unrestricted exhaust and intake. I had a few problems that really pushed me to sell it back in the day that now (ten years later) I don't think were too big of a deal.
I could write a novel here but I'll touch on some of the main issues that you could be faced with motor wise.
1. Injector pump. After 93 the pump was electronically controlled and I feel GM did a great job matching the DS4 pump to the motor no complaints there. However the Fuel Solenoid Driver (about the size of a deck of cards) was placed on the side of the pump in an effort to keep it cool. This was a poor design and often these drivers would fail from excessive heat giving the same symptoms as a failed Injector Pump. The only fix I found was to relocate the driver completely OUT OF THE engine bay. The other kits that put it on the intake housing actually create more heat I know becuase I have a heat gun and verified it. The only kit that moves this part correctly is the one from Heath Diesel. I believe the injector pump should last 100k miles or more reliably imo.
2. OPS. The oil pressure switch is prone to failure but they are easy to change so keep one in the glove box and understand their function. Once they fail you may or may not ever know until you go to start the motor after shutting it off. Hard starts or no starts and a hesitation at high rpms are the symptoms. There must be oil pressure for the fuel lift pump to turn on and supply fuel to the injector pump. It took me awhile to figure that one out (DOH)
3. Broken crank. The cranks on these motors are tough, but a defective harmonic balancer will cause them to weaken and break over time. Feel around on the balancer often and check for cracks in the rubber. Some last a long time others split and loose balance often without the driver noticing.
4. Cooling. You'd be good to go here. Early 96 and older had a poor cooling system. A 98 will have all the upgraded high flow pieces just make sure you replace the water pump with the same year pump and not an earlier one! A 99-00 cooling fan is well worth the money if you tow a lot. I talked to Bill Heath and he said the 6.5 heads have been know to crack at anything over 217* :Wow1: DON'T overheat this motor LOL.
5. Glow plugs. Replace ONLY with the OEM plugs and nothing else. Cheap plugs like autolites or champions will burn out quickly and often swell on the end making them extremely difficult to remove.
6. Oil leaks. Get used to them or buy the upgraded lines/hoses.
Anyway thats all I can think of at the moment. The 2500 will have a really strong axle whether it is a light 3/4ton or heavy. Also both transmissions (auto or manual) are winners if you keep them healthy. Good luck if you have any specific questions please hit me up I'll try my best to help.
Andrew
EDIT:
www.thedieselpage.com (buy their books!)
www.heathdiesel.com
www.kennedydiesel.com
^ these guys have seen it all and are a wealth of info.