along with safe and adaquate equipment
the last thing i would call most roll-back trucks and their drivers are safe and adequate. i'm surprised most of these people can breathe on their own, let alone safetly drive a truck with another vehicle chained to the back. i cant tell you how many times ive seen one of these clowns flying down the road with a car on their deck being held by nothing but the winch cable. i will drive my tractor somewhere before i would ever let some rollback driver take it for me. i drive a heavy haul lowboy, and know how to safetly transport machinery, these guys dont........
FYI....u-haul trailer tend to be on the HEAVY side (like really heavy), so that they can take the abuse of rental customers. they also tend to only have 2 "tracks" to drive the vehicle on (no center, just decking for the tires), so be sure you tractor's tires will fall on these "tracks". my buddy has on old ex-uhaul car trailer, and you cannot fit a fullsize truck on the deck, its just not long enough, and nowhere near 16ft, maybe 12ft. also, u-haul will ask a ton questions about what the tow vehicle is, what is going on the trailer, how much weight, etc, and if it doesnt pass their computer generated formula, they wont let you rent it, and if you lie and get in an accident, they sue you.
i had to move once, and rented a 24ft budget van (international truck), and loaded an old toyota pickup in the van, screwed wood blocks to the vans wood floor as wheel chocks, and used ratchet straps attached the the "e-track" that runs along the sides of the van body to secure it. it rode great. i then also towed a fullsize dodge truck on a borrowed car trailer behind the van. it went well.
i would have no issue putting a small tractor in the back of a box van. these trucks are rented by businesses for the purpose of being loaded up and used commercially day in and day out.