I have towed double since 1993, 18 years with an Eagle 215SD and the last three with an Eagle Super Lite HT 26.5 RLS. Biggest one towed was a 22' 5,000 lb boat and trailer combo and we towed it with no problems. Just make sure you get a hitch installed by a professional welder rather than a bolt-on hitch, no matter what the weight or length of your boat and trailer. I know our state is pretty generous with its towing regulations, but the length can be up to 85' for a trailer and boat but all trailers must have brakes. I have had surge brakes on all my trailers, except the first one. As far as backing, I have not yet had to back so can't help you there. I don't know if you need sway bars, but if you put them on, probably won't hurt. If you have a travel trailer rather than a fifth wheel, I would recommend them on both trailers.