VP-44 Trucks. 98.5 - 02 2500 and 3500s.
You have a couple of things to look for and consider.
First and foremost, you need to check the condition of the lift pump. There are 2 pumps on these trucks, the lift pump (which supplies fuel up to the engine) and the injector pump (which actually injects fuel into the engine). These fail "generally" one after another. The lift pump will fail, which provides less fuel to the injector pump. The truck will still run, but will eventually have such a difficult time pulling fuel that it will kill the injector pump.. A new injector pump is going to cost you in the neighborhood of $1100-1500, so it isn't a part to be taken lightly. The best way to check the lift pump is to check the fuel pressure at the injector pump. There is a small shreider (sp?) valve that is the easiest poin to check out. You want around 12-15psi min. at idle, and no less then 8-10 at full throttle.. according to cummins. Obviously, the less the fuel pressure drops during a wide open throttle run, the better.
Another thing you want to check is if the truck has a "53 block" or not. This is something you will want to research.. The short and skinny is that there are several trucks that had a different engine casting then what Cummins requested.. Which can, potentially, cause the block to crack. You can check for a "53 block" on the side of the engine.. Research it here and through google, and you will have more to read on the subject then you probably care to know.
There are a few transmission issue to look out for. The automatics almost always require SOME modification, and there are a few years of the 6-speed that have smaller input shafts. Also, if your goal is flat out HP, you might want to read on the differences between an SO engine (standard output) and a high output engine (HO engine).
Other issues to look out for? The newest truck is going to be around 7-9 years old... So, expect to check things like tie rod ends, brakes, clutch, etc. etc.
These trucks are the "black sheep" of the dodge world. If you can get a good price, they are generally worth it.. Otherwise, look for a nice low miles 94-98 (12 valve) or the new common rail diesels (03+). For advice on what to look for on those rigs, check the appropriate year forums on this site.
Hope that helps!