Originally Posted by BuzzardsGottaEat
My serious advice: It will cost you a TON more in the long run to get two trucks than it will to pay off the first one in the configuration you know you want. Even if you only lose $1,000 on resale (not likely) you still may end up starting all over with a brand new truck, again. . . Just drive em both and get what you want the first time. Resale value is higher on DC that AC I believe as well. Not that it will make much difference if you end up buying twice.
Seems to be going against the grain, but "been-there-done-that", and fully agree with Buzzard. Always look out at least 3-5 years on what you need, otherwise you end up in a trade deal where you will lose money over doing it right the first time.
Other factors definitely need to be considered, but since you posted as "resale..", the financial aspects are high on your priority list.