I have been trailering something or another now for more than 10 years. I am 43 and we bought our first camper when I was 30 and a cool kayak trailer about that time too. I got my first boat with a motor when I was 32.
I have noticed that pound for pound towing a boat is much easier than towing a TT even the pop up. With the boat I have no WDH, no sway control and so far all on 2" balls. My current boat loaded wet with fuel, freshwater, gear and trailer weight is pushing 7,000 pounds. It tows fantastic and with ease on my Tundra. Now it does push the 4 Runner around going down hill in the mountains..I have towed it short distances with it and the 4 Runner has a V8 with tow package, transmission cooler and so forth.
I have wondered why TT (rvs, campers) tow so "crappily", if that is even a word
, without all this extra gear of sway control, WDH and so forth? I suspect it is their shoe box shape that sets them up for sway and the other issues. Boats on the other hand are more aerodynamic on the trailers compared to RVs. Maybe it is the mass of the boat itself? But, then again mass is mass when it comes to objects in motion, stopping and so forth. My current boat though is taller on the trailer than my soon to arrive Roo. This is just a random thought...before I head off to work.