An auto car on a tow dolly?

dont have to be uhaul, can be any company, trailer has electric brakes, and if you have someone with a full size truck, pick the trailer up with it and then transfer it to your dakota, problem with most tow dolly, when you back up with them they will dent your car fenders thats on them, have a 87 charger i just pulled and put a big crease in the fender trying to backup where i backed it in the garage, the 83 plymouth scamp and rampage was 2200lbs,,, thats my opinion, but they are like assholes ,everybody has one, i would do what you fell more comfortable with, you have dead weight pushing downhill because most dollys have no breaks, make sure the rearend is good and axle bearings, and rear breaks on car you are towing are good, and rearend has fluid, any of those can make towing a car a long trip trying to fix them on the road.
I can add axle gear lube to the list of stuff to bring along, gramps has a whole drum of it. I'll also gauge the amount of crest to the dolly hooked up to my truck before I rent it, so I have a good idea where it comes to the fender. But yeah first I'm talkin to a family friend, he has a big diesel and pretty sure he has a trailer so im seeing if hes open to the idea. It'd be a good long drive so we'd be trading off driving