I towed my ITR back from Portland with a Uhaul box truck and dolly.
As long as you drive the speed limit, it's not that big of a deal.
Granted, this wasn't the first time I was towing. Watch the episode of Family guy where Peter tries to back a boat into the water. Learn to go forward to straighten the trailer, and to pre-turn the trailer.
The only thing I have to say, the E350 that I was pulling with had a nasty shake at speeds above 55 mph so that was how I knew I was going too fast.
Oh and crossing the border sucked ass. The lady at the border was ignorant about Uhauls.