Towing a boat behind a 5th wheel is no big deal if it's legal and you keep it reasonable and have good equipment. Our 5'er was 28' and the boat about 20' with the motor etc. Total length was around 66' if I remember correctly. We were allowed to do this in Alberta, Saskatchewan and Manitoba with a max length of 72' in Sask. All prairie provinces and usually pretty flat country. I only had a problem a couple of times where I had to drop the boat to maneuver the truck/trailer through a tight spot. Other than that, it was great! Get to the lake, drop the boat in the parking lot, park the trailer and go pick up the boat. You can take every thing with you.