Another vote for the newer style truck, as new as possible. Modern drivetrain, functioning climate controls, quieter interior, more creature comforts, etc. What you DON'T want to hear from the family is "Oh, we're taking the old beast on a trip again?" after spending whatever money to build it just the way you want it. Old trucks are..... old. Squeaks, creaks, rattles, barely adequate a/c, road noise, wind noise, wind noise, and more wind noise. Spend 6 hours driving something like that to a destination and everyone in the truck is just plain worn out by the time you get there.
Granted, an old truck can be updated, made quieter, more modern, etc. But, since you are not doing the work yourself, you will pay MORE than buying a newer truck to have this done.
I also like the idea of having a newer truck with the modern powertrain originally equipped simply for the reasons of repair/maintenance. If you break down somewhere or need repairs, even regular maintenance, it will be easier in the end for the shop doing the work to get the parts needed. No mismatched stuff, no hard to find, or "My computer doesn't show a 6.0 engine for a 91 Suburban. It says 5.7 though..."
If I were in your shoes it would be a mid 00s Burb, 3/4 ton with either the 6.0 or 8.1 gasser and 4L80E trans. D60 front, 14bff rear with 37" tires and 4.88 (maybe 5.13) gears. Lift as low as possible, trim body/add flares to accomodate. A good quality on board air system or CO2 tanks to air the tires back up. A good front winch bumper and winch and rear bumper with spare tire carrier as well as some rock sliders with built in steps for easier cab access. Mix well and enjoy.
Oh, and it's true that awesome parts can sometimes make up for lack of driving skill, they can also get an unskilled driver into trouble. Take the time to learn how to drive your truck. Know what it can and can't do before finding out the hard way.
