1. don't get a normally aspirated Uhaul. The 500 miles from Tulsa, OK to Houston, TX I drove one was the worst 500 miles of my life. 24' box truck with a 16' trailer and we couldn't go over 50 the entire way. not to mention it got 3-4mpg. ugh. the heater was also stuck on broil and it was over 100deg that day. Needless to say, we had several things to say with Uhaul when we got to Houston.
I'd recommend spending a couple more bucks and going with something else if they try to give you a beater uhaul. we were getting passed up and down hills all day long by Penskes and Ryders with AC and cruise control.
that said, get a trailer, not a tow dolly. much easier for a rookie to pull because of the backing issue. another option is the "hire a friend" approach. not sure if there's an airport near either end, but maybe he can throw a few bucks at a friend to drive the camry there and serve as roadside assistance if the truck has a problem.. then fly him home.
for the cost of renting a trailer 1-way, it may only be $50-100 more to do that and I'd feel much safer in every aspect if that were me. (then again when I was moving $100 might as well have been $100,000 cause I didn't have it!)
advice for pulling the trailer...
1. check tires.
2. check tie downs.
3. check lights.
4. check them all again before leaving.
5. after 5 miles, pull over and check it all one more time, incluing trailer ball/linkage for loosening.
6. check again after 50 miles and every time you stop thereafter.
the 5-10 minutes you spend with that will greatly outweigh the nightmares of losing/wrecking a trailer or having 3 flats in less than 50 miles like I did last month.
Last thing is to plan the trip timing (and throw in time for delays!) so that he's not driving in/around Chicago anywhere near peak traffic. I hit Houston traffic at 5pm on a Friday in that uhaul and wish I'd have just pulled over for dinner and waited it out.
