I have a 95 GMC 2500 (basically the same truck) and love it. However, I don’t think I would love it if I were in a hillier or snowier region (I’m in FL). It has under 150k miles on it, and I have a mechanic nearby who keeps it in good shape very reasonably. I’ve had to have coolant or AC something fixed about every 2 years (2 years ago I had all new AC system put in, just due to old truck-itis), but not the type of thing that will leave me or the horses stranded on the side of the road. I also had it repainted as, yes, the clearcoat was starting to peel horribly. The dash is cracked from years of UV exposure…I actually think that issue is going to determine the lifespan of my Bessie.
If you regularly park in pastures and/or have to deal with snow, go for 4WD. If you have hills/mountains to traverse regularly and pull more than one horse in a light 2H trailer, get a newer or 3500. That era of 2500 are good, but their power up hills with 2-3 horses in a 3H trailer leaves something to be desired.
Oh, and pretty sure mine wouldn’t pass an emissions test at this point! I’m hoping to nurse mine along until my 18-month-old is done with daycare/preschool, and then I’ll start looking for a new(er) truck. I’m kind of fond of mine, though I don’t really get attached to vehicles!
On the price–I bought mine 10 years ago, so no input there. However, I do think the ‘clunker buyback’ pushed prices up a bit for a while. Not sure if that had ripple effects this far out.