Happy to report that tractor made it to the new property in a completely uneventful manner.
No problems towing with the EcoDiesel(19 MPG up, 25 back w/ empty trailer!), only thing I noticed was a slight vibration, maybe ~3Hz that seemed to come and go every 2 miles or so. Thottle, uphill, downhill or turning didn't seem to change it so I'm just assuming it was road surface(there's a section of I-5 south of seattle that'll rattle your teeth if you have just the right wheelbase).
All the straps held well, checked 2-3 times along the drive at various rest stops and hubs were not overly warm, overall pretty happy with the setup. Also having undone/redone the binders many times they go on much faster now.
Cheers for all the feedback, definitely appreciated and hope it helps anyone in the future.