I pull a Kwik Kamp camper which is 36 inches wide with the Road Glide. With passenger. That is about as wide as i will ever tow. Only thing I can advise on is to to keep the trailer about as wide as the handlebars, I tow a canoe on an extended harbor freight trailer and have a closed box clamshell too. None wider than the bike. Towed for many thousands of miles on 3 different Harleys and never had a scary moment. If it sways, move the weight backwards or lengthen the tongue. Those roof top carriers are very flimsy. Trailer weight on the hitch is around 30 lb. I use a MC Hitch which is way better than any of the others I tried before .
Do it yu will like the added comfort of more stuff.