Listen to burningman on the 53 block
99 with long beds are harder to find, but not impossible. Autos are more abundant than the manuals. Which are you looking at?
I assume by "towing a 5th" your concern is all the stress on the truck. True, but how many mile did the PO actually tow? I would be very weary of buying a truck with a 5th or gooseneck hitch in the bed. Those hitches are great for towing very heavy loads. The Cummins can tow 30,000 lbs, way over the rated limit, and there are people who will do just that.
Though, my truck has a gooseneck hitch I put on and have never used it. I went another route..
Other than the 53 block, the Cummins is a great motor. The tappet cover will leak, so see if that has been replaced, the original ones just dry up and crack. You will have oil leaks, this is not detrimental, actually normal for diesels, but you also do not want one that leaks like a spigot.
The injector pump is the VP44 and will fail. $1,400-1,500 for a new one plus labor, but not hard to do yourself.
The stock lift pump (what sends fuel from gas tank (diesel) to the injector pump) is junk. You want to see an aftermarked one which will be installed on the frame between fender and frame in front of the left rear wheel. FASS or Air Dog is typical. There are other good fixes, but these two are best.
The drivers seat cushion will be worn out. Genos (genoes) garage has all these parts. The dash board top will be non-existent or will have been replaced.
If 4x4 you will want the more rare CAD front axle, otherwise the front axle spins all the time into the diff and the transfer case.
Back to the trans. On manual there are a lot of issues with the NV4500 5 speed trans. The 5th gear was a major issue and cause of many trans end of life. The 5th gear nut can be fixed. Ask for proof of this. Otherwise budget the price of a new trans in what you plan to spend (about $3500-4000 installed) The trans itself is about $1.500 for a rebuilt NV4500, there are no new ones.
There are a lot of bad rebuilt units out there. I got one where the KY rebuild shop welded in the 5th gear, so that one was ruined after only 80k of driving. Just avoid anything that originated from KY to be safe.
If it has been "chipped" then that may or may not be good. Depends on the owner. Chips are Edge programmers or other brands that alter the CPU, mostly increase the fueling to the injectors to increase power. More power means more stress on that already stressed trans pulling a giant 5th wheeler.
I see trucks pulling giant trailers up mountains blowing by me doing 70-75mph. The cummins can do that, but the trans is screaming, help me. I would not want to buy that truck.
Go look at dodge cummins forums, or do internet search for info on that 2nd gen truck to get an idea what you are getting into. There were a lot of issues with the truck, but if those were fixed then would no longer be an issue. Some people fix them with upgrades, some just replace with the same problem part and hope for a few more miles.