My 96 S-10 has been a great little truck. It has the 4.3 V6 in it. I've towed a trailer loaded down with motorcycles for years. Loaded and unloaded bikes in the back of it more times than I can even count. I added one helper leafs on the rear suspension and it helped alot with hauling bikes. Good, solid truck still with 250k on it.
But, if you are looking for the lowest maintenance truck out there, find a used Toyota Tacoma with over 100K on it. They run forever. A friend of mine had 400k on his late 80s model when he sold it. Still ran great and the person drove it for a long time after that. Who knows, the thing mite still be running.
You're best off with a chevy S10 with a V6, make sure its a V6 or a Toyota Tacoma.
But who knows Justin. You're Mr. Money bags. After this track weekend coming up you may go all out. Fullsize Tundra with a V-Nose 6X10 Hallmark enclosed trailer with racks for your spare wheels and tires, full tool box, tire warmers, tons of spare parts, brand new pit bull stands, built in work bench, tire changer... the works ya know.
Go ahead buddy, take a hit off the track pipe.