Towing boats behind 5th wheels is just the way it is around here. We have a 75' length limit and there are very few rigs going down the highways that don't have a boat, a jetski, or a bike rack on the back. It goes on for 5 months straight. I've never had to worry about backing the thing up, you just need to know where your going and don't drive yourself into a pinch. I don't think its any different than all the other stuff you need to know before towing (like not whacking your cab corners trying to back up). Maybe its not for everyone but I had to make that decision myself.
2004 Wildcat 28BH
2012 Ram 2500 CCSB 6.7CTD