As far as what you should look for, it depends on the price and what you're buying it as.
I'd guess since you keep bringing up the fact that the sales price is a third of what the guy put into it, and that the guy paid dearly, that the sales price is high, and what you're looking at is a fully restored truck.
If the truck is in fact "fully restored", then i'd look at it like i'd look at a new vehicle.. because thats what "fully restored" means.
Every part on the truck outta be clean enough to eat off of. Check for rust (or shoddy repairs) in the usual places you'd look for them in an AD light duty truck.
Then theres all the normal things you should check whenever you buy a used vehicle (like water, oil, stuff like that)
The big issue with those big trucks is the brakes, since they like to rot out from the inside out.. but if this truck is a "fully restored" truck, all that stuff should be new.
The point I keep thinking about is, you don't like the color, the truck sounds expensive, and your already thinking of swapping the tranny out.
In my humble opinion, if you're going to pay premium jack for a 1.5 ton, it really should be just the way you want it, otherwise, you might as well grab a solid $300 (or less) truck and do it the way you want it. (and probably save a bundle, too)
There was a thread on here that addressed the "how do i shift the two speed axl" question.. you may try the search option to find it.
Keep in mind there are TWO search features here, one is the google search, the other is the built in UBB Board search.. try them both (one seems to work better than the other for different things)
I personally have no idea how you shift a two speed rear.. but somebody around here i'm sure does, or can point you to the thread that has that info.