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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Jake one of the other advantages of the diesel that has not been talked about is resale value. Their are so few diesel truck for sale, that I could go out and sell mine after one year and make money on it. (V10's? No so...)If you go diesel, the dodge cummins is by far the best engine, but the truck itself IMO sucks.

I went with the Ford for 3 simple reasons.
1. Resale
2. Quality (I know this is funny, but they are the best of the Big 3)
3. Style

When I went to the dealers and researched the market extensively, it was a no brainer to go diesel when towing.

Have you looked at the 8100 in the HD? I would not even consider the 6.0L