I like driving, too, more so if I'm by myself, so Wanderer's hotshot hauling idea sounds cool.
I looked this up
http://www.overdriveonline.com/hotshot-trucking-how-to-start/
I recently bought a house on 20 acres in a rural, yet economically busy part of the state, planning on renting it out for now. In a year or two, might consider this as an option and move there myself. I have done a lot of hauling on flatbed trailers, loaded a lot of box trucks for my job and other projects, and pulled a lot of weird loads on my bike trailer [180 pound maximum, 3-60lb bags of concrete, small cement mixer, 100 gallon cone tank with steel stand, 4 bundles of 16' siding(I made a tongue extender) 4 sapling trees with a tandem trailer set up I made, etc.]
The load securement class sounds interesting.