Originally Posted by Hotrod_Lincoln
DOT medical card- - - -gotta have one to drive anything commercial over 25K pound gross weight.

26,000. Keep my 3 dump trucks registered at 25,900lb.

If I was considering something like you’re describing, I’d be more apt to get into hotshot hauling. Big money in transportation/shipping right now. Grab a Ram 3500-5500 with a steel flat bed/gooseneck and a trailer and go see the country.
Either that or a small (9yd) dumpster set up and rent to contractors and homeowners.
Being that you’ve worked IT jobs apparently, you’ll probably be shocked when you realize driving a truck isn’t exactly gravy.