Being from Devils Lake you see these every weekend. I used to do the same. Originally with a 1/2 ton, 28ft. fifth wheel, and 19' Pro-V. Later went to a 3/4 ton, 32' fifth wheel, and 20' Lund. Could easily pull it at 65-70. You really didn't know the boat was there. The one thing I found when doing it was a 1/2 ton is way too light. When you'd get on a road that was worn things would sometimes start swaying since you have 3 items with different wheel tracks. The half ton truck's suspension just didn't cut it. When I went to a 3/4 ton it was night and day. Way more solid and felt much safer. As for backing up, you don't. You make sure you don't get yourself in a spot where you'd need to. Even semi drivers who tow triples don't back them up on a regular basis. But after having done it for years, it's really not a big deal and easier than you'd think. Especially in the more rural states like ND, SD, & MT where I usually went. Not sure I'd want to deal with it in the traffic of bigger cities though.