A couple years ago I helped a friend move from here (near Seattle) to south of Denver, taking his collection of '55-'57 Chevy stuff along.
I towed a '57 Chevy 2-door wagon down on a dolly and a '56 Nomad on a trailer. Most the stuff went that way, trailered or dollied. A '57 Chevy wagon was driven down. His machine tools and spare parts went in a big trailer pulled by a semi he was given for the move.
We spent months checking fluids and brakes, replacing tires, greasing bearings, and that kind of thing to be ready. The actual trips were almost completely uneventful as a result.
My advice? Make sure your tires and brakes are good. And start driving the trucks regularly now if you don't already. Make them tell you what doesn't work or is near failure, so you don't have to find parts to fix it on the road.
Tell me more about the schedule. I'm tempted to offer to help drive...
