Too many worry warts here. My biggest concern would be whatever Uhaul you are renting being too anemic to tow a trailer without being a burden on your trip.
If you're getting a moving van AND towing the trailer, consider a Penske or similar moving van on a bigger chassis.
I got sick of the Uhaul junk and runaround years ago. Last time I did what you're planning I got a big Penske truck class 6 or whatever it was and cruised at max speed the whole way with snowmachine trailer in tow.
Nice to not be dogging a u haul turd all loaded down. But maybe u haul is better now?
Haven't moved with a moving van since 2011