Never have towed with a short bed. Have always had and always will have a long bed, plus Crew Cab plus Dually. There are usually only the two of us but a long bed crew cab provides lots of room for all that extra stuff that makes the trip more fun.
As a daily driver the empty crew cab dually is very comfortable. Sure the ride can be jolting over rough surfaces but most of the time it's not bad. People tend to get out of your way. I've never had an issue with parking since I usually park far out in a lot and like to walk.