I've seen some pretty cheap tractors rigs compared to newer diesel p/u's. I wonder how much insureance is for a tractor rig with a flat bed trailer? Getting a CDL sounds like a good idea. If a guy had two or three friends that wheeled alot and could split the cost that would be ideal. The problem for most is where to park it. Having several acres isn't a problem but I can hear the homeowners association bitching now!
But on the other hand, these newer pu's can haul two maybe three rigs pending type of trailer.