Now days, with backup cameras, hitching/unhitching is probably a wash. I may not be able to do it quite as quick as those with fivers, but I've never dropped my trailer on my bed rails either. Watched that happen to an experienced old hand last year. Travel trailers track truer behind tow vehicles too, which is usually an advantage, but not always. Travel trailers are almost always lower than fivers. No steps inside a travel trailer. They're cheaper too.
Fifth wheels, which are typically taller, offer an open, airy experience, much better (for me anyhow) on extended trips or full-timing. They have much more built in storage. They offer more interior living space foot for foot. More stable towing, especially in windy conditions so I'm lead to believe, and do.
As I age and consider longer adventures, fivers (and motor homes) get more attractive. But I'm still young enough to be bound to a job and like the idea of bringing toys (bikes/motorcycles/atvs/canoes/etc.). I also use my tow vehicle as my commute vehicle, and thus settled for a half ton. Totally unsatisfactory for towing a nice fiver.