Already having my Caddy, I'll take a couple trucks...
The hauler: 1992 Jeep Commanche 4x4 pickup. Long bed, HD "metric tonne" suspension with 4.11 gears, 5-speed manual, four-cylinder engine, A/C, cruise control, tilt column, bucket seats with console, and full gauges with tachometer. No other options--no carpet, no power add-ons. Rhino-Line the box, add a set of 30x9.50 Treadwright tires.
The muscle truck: 1992-96 Dodge Dakota pickup, 2WD. Long bed, start with a V6 or V8/5-speed, a Southern truck with no rust. It gets a 408ci 360 Magnum stroker good for about 500-525HP (dressed to look like a stock 318), trans would be a double-overdrive T56, stock rear axle with a Truetrac limited slip and 3.90 gears. Lower it an inch, run flat-black "soft 8" steelies, HD swaybars & shocks. Hide a class 3 hitch behind the licence plate holder.