Considering that our driveway looks like a truck brochure from 2000, I think that we'll stick to that theme.
I would order a GMC c3500hd crew cab with a Monroe 4wd conversion in full trim. It would be black with a polished aluminum flatbed, probably 10'. I would order it as a diesel and immediately swap it for a Cummins and regear the axles to make the Cummins happy. The interior would get seat heaters front and rear as well as a Denali center console and metal inside door handles. The entire interior would get ripped out and sound deadened. The windows would be tinted to appear stock. I would convert to composite lights with the matching GMC grill but it would get a billet insert painted black. A full trim diesel bumper would have to go on. In the 90's Pro Comp offered a prerunner bar that attached to the factory bumper and that would happen with 8" stainless Pro Comp lights. Alcoas, enough said. Chrome tube steps. Denali heated mirrors. If I could afford all of that then I could obviously afford the best air ride that 2000 could offer.
I wouldn't stop there though. I would also order a 2000 crew cab short bed K2500 with the 454, NV4500 and 4.10 gears. It would be odd because I'd want heated leather seats and power windows/locks but a rubber floor. It would get tinted windows and a spray in bed liner. Spiral gray was a 99 color but I would try to talk them into it.
Because I obviously have cash falling out of my ****** I can afford a 3rd one. This is another ccsb but this time it is a C2500. I would get the sound deadened full interior from the c3500hd, diesel bumper and cheapest drivetrain that I could buy because it would immediately come out. It would get a 4/6 drop on bags, 17s, the 405 hp Z06 LS6, a T56 and some form of boost. I would also do a step side bed with a step shaver/roll pan/hidden hitch. A flush mount hard tonneau would be required. Keeping with the Corvette theme, it would have to Nassau Blue