I just played with this trip in my map program.
It looks like nearly 2,000 miles if you avoid the Interstates and at least 40 hours driving time assuming you'll be running slower than most the traffic. And it estimates $600 for fuel each truck...
Add regular eating and nights in hotels and this is an expensive move.
As much as this seems like fun to me, I wonder if you should look for some other way to get it done.
