I had a 99 24v with 250k miles on it. I bought it with higher mileage and the previous owner had already went through the pain of the transmissions that go out at 180k and the lift pump and injector pump that went out on him. Was a nice driving truck, however I never got the fuel mileage that some BSers claim. I do miss having a strong tow rig with the 8 foot box, however the truck felt like was on the verge of needing a lot more repairs so I sold it while the going was good.

Later a 97 12v truck fell into my lap for cheap. I had just shy of 290k miles on it. Everything was worn out and was going to take at least 5k in parts to get it roadworthy. Engine started having problems, I was worried it could be the injection pump so I got rid of it before putting a dime into it.

Nicest truck I drove was my buddy's 01 2500 with the v10 and stick shift. Thing drove wonderfully. 12mpg but at least no diesel-cost repairs to have to worry about. FWIW, I work at a heavy duty truck/trailer repair division of a transport fleet. Nobody drives a diesel as their daily driver except the boss who's always having problems with his.