We have towed boats behind our FWs since 1993, when we bought our first FW. Boats ranged from a 19', very light, Byliner Capri to a 22' Sea Hunt Escape Dual Console Salt Water fishing boat whose weight on the wheels, while hooked to the FW, was 5,000 pounds. No problems and have been lucky enough to have not gotten in a position where we had to back up with all three items. I could turn around in a road if it was wide enough but have not driven on a road that wide. Our current sit-up is a Jayco SuperLite 26.5 RLS that is approximately 30' long from hitch to back of bumper and we hitch a Crestliner Super Hawk 1900 behind it and go camping and fishing. We do this at least three times each year when going to Grand Teton National Park, stay at Colter Bay campground and fish Jackson Lake. Needless to say, don't use a bolt-on hitch, go to a professional welder and have a hitch welded on to the FW and, if necessary, have them reinforce the frames toward the axles.