The problem with a long bed truck is if it's mounted on a crew cab chassis. At 22' long, maneuvering such a long wheelbase vehicle is very slow and awkward.
I tow with a F250 crew cab with 6.5' box, and it's certainly long enough of a vehicle for me. I had my 24' boat in my driveway this weekend, and the whole rig was about 50' long.
Most of the time, I still take up two parking places as I'm too lazy to go forward and reverse 5-6 times to get it straight.
My SWB crew cab is long enough for me. Trick is buying a fifth wheel trailer that is designed for SWB vehicles. Most of the new designs will turn 77 degrees.