Long distance dolly towing

I rented a u=haul car trailer a few years back to go from South Dakota to Kansas and pick up a Shelby charger(pretty much all flat land). I could have rented for one way and picked the trailer up down there but it was cheaper to rent it for the weekend and return it where I rented it, in my case. I read the fine print online "they will inspect tow vehicle..." so I went and put new tires on my 98 Dakota (2 wheel drive, 3.9 auto), they never even looked at my Dakota, the local U-Haul renter is a friend so that may have had something to do with it. I used to tow a 73 Chevelle on a homemade car trailer(no brakes)going was not a problem, stopping was problematic at times.