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In your case, I would highly recommend the diesel. It will far surpass the V10 in fuel economy. Like you said, it will cost more, but it will maintain it's resale (as you have learned). That alone speaks for the desirability of diesel over gas.
As for SRW vs. DRW, you will get lots of debate. I went SRW because it was more than enough capacity for our trailer, easier to maneuver, and costs less for tires (4 as opposed to 6). Besides, who needs training wheels on a truck? (That should get me in a lot of trouble!)
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