To me the best thing about a suburban is that there's generally enough room to put everything you need inside without "mods." Then it still works a family vehicle/people hauler or whatever when you're not "overlanding."
I would take a good look at the cooling system. Make sure the intake gaskets aren't leaking, the goofy heater hose connector on the front of the intake isn't leaking (a hose barb works great here), rear heater hose plastic "T" fittings will generally crack and break, ditto the plastic heater control valve. If there's a rubber heater hose block off on the right side radiator tank under the radiator cap, get spares in the "help" section of your FLAPS. It will split and leave you stranded at the worst time.
Brake system troubles are notorious on these rigs. You don't need a GMT800 master or any other hocus pocus. The rear brake drum hardware has usually been assembled and adjusted incorrectly at some quickie brake job place. Take your time (and maybe a service manual) and do them correctly. Replace the old rubber hoses and flush the old fluid out. It will stop fine.
Avoid cranking the torsion bars too high and your ball joints and cv axles will thank you. Your 99 should already have the good front axle actuator, that was a problem on the earlier GMT400's.
When your rear AC stops blowing cold and the front still works you'll need to change the expansion valve at the back. It will be corroded to the evaporator core and the rear AC lines will have to be changed. At this point you'll probably be ready to move on because the cost of the AC repair will eclipse the value of the truck...
All that said, I still like them. I've done nearly a million miles in the GMT800 Suburbans and can't say I like any of the newer ones any better!