At one time, I had a 95 Chevy 1 ton with the peice of crap 6.5, didn't like my 38' enclosed. Beck in 05, I bought me a new 04 C4500 Kodiak.Good thing I did b/c I met the woman of my dream and she wanted to race. So we had to buy a 48' to haul both cars in. Weighs about 20k plus the 11k for the truck. I wouldn't do it with a 3/4.
I have the 38' for sale if he is looking for a trailer, it can be towed with a 3/4 ton.