Wow!
I don't envy you the task you've set for yourself!
Over the years my brothers and myself have towed, pushed, or dragged dozens (probably hundreds) of vehicles. Almost all were short haul (under 30 miles). I've chained 'em, used towbars and car dolly's, and finally bought a used 18' dual axle trailer. It was in need of repair - the decking was shot, the wiring was ripped to shreds, and the tires were iffy, but over the last couple of seasons I've put it back into serviceable condition. I welded on a new receiver, replaced the spotting wheel, added a cable hoist (from a boat trailer) and covered the front deck with Diamond Plate so that I had a safe place to step.
There is NO WAY I would undertake moving a vehicle more that a few miles without having it on a trailer! Especially this time of year.
Good luck and let us know how you fared!