jeremy's situation leads to an interesting aspect as well. He's selling his race car, getting his MBA, and has....a truck that rides like it has concrete blocks for springs...

so....be sure of your long term plans, or, be ok with the used value you will get back selling it if you have to.

Also, high mileage versions of the HD trucks rattle and shake and give europeans more fodder for their "American cars are peices of crap" claims, LOL. (They destroy themselves, essentially)
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part of the reason i think a 1500 with the 6.0 is the best compromise. a 2500 over a 1500 with the same trim will cost a couple extra grand right? so why not save that couple g's on the truck and spend it on an alum trailer instead? you'd have a far better DD, and a NICE trailer that even stays cool in the blazing sun.