Hi jdl, I hope your Mom let you get that truck! We towed a 54 Chevy 3100 from St. Louis to Florida on a U-Haul trailer, and another 54 Chevy 3100 from Kansas to Florida with a U-Haul trailer - both times the trailers did just fine. I don't know if U-Haul has the 3100's in their database as acceptable vehicles to tow on their trailers. Both times we told them that we were towing a different vehicle on the trailer (a newer smaller car). This is not to tell you what to do if you use one of their trailers, only passing on my experiences with using their trailers. Good Luck, and congratulations if that's they truck you're getting! I got my 54 Chevy 3100 when I was in my teens and I still have it.
Samantha
I used to work for u haul (10 years ago) and they will not let you tow a full size truck on their car trailer (auto transport) so I agree just tell them you will be towing something else on it. The truck will fit.