I tow a 28" behind my 36' MH. Yes, all I see in camera is trailer. Issues I have. Loaded trailer weighs 8200 lbs. Tonque weight is 1280. On some roads I would experience some porposing so I bought a
Trailer Toad which fixed that problem.
As one other OP stated many states have max length laws and some are absurdly short. I looked at a chart once and a couple states were 55'. Personally I don't worry about it. I know a lot of racers who have 35'+ MHs that tow 24-32' trailers.
The biggest issue to pulling a trailer vs. a 4 down toad is you have to plan ahead. Getting around on two lane roads can be a little difficult at times when you have to turn at intersections.