Obviously more than what you stated your price range was, but I'll share my only diesel experience. Last year I bought a brand new 2014 Dodge 3500 2wd Tradesmen dually for $38,995. At first I was very happy bc of all the good I'd heard about the cummins. I bought it solely bc I couldn't find any other dealer close to that price. All other brands were at least 10k more, or used and 100k miles. In the 13 months I owned it, it randomly would not start 10 different times. The radio that controls half the trucks functions would go in and out. The truck had a dead pedal and would have a few second delay if you stood in it. I also had 4 different CELs all of which the dealer(multiple) told me it would be a few months before they could run them and tell me what was wrong with the truck. So I would have to go to Autozone and run the codes, then back to the dealer to get on a waiting list to be fixed. At 40k miles I traded it in with bad cats and a leaking pinion seal.
If they wouldn't fix it new, I couldn't risk out of warranty issues, so I picked up a 2015 Ford F350 CCLB dually with the bigger turbo and upgraded trans for 40k. It rides better, pulls better, turns better, stops better, is quieter, and looks better imo.