Having just retired after 25 years driving one of those big red ladder trucks too, we went with the 5th wheel. At first we were looking at motorhomes till my wife stepped in a 36ft 5th wheel. she was floored with all the extra room over even a 40ft DP we were looking at. Plus I needed (wanted) a new full size pickup. We do tend to stay a week or so at a time, but not always.
as others have said, it all depends on what you can afford and what you want. We find that we tend to pull over at least every 3 hours anyway to let the dogs out and for me to stretch, so you can eat and use the head then. We pull over wherever we want. My wife likes using our trailer compared to rest stop or other bathrooms.
And yes, besides maybe leveling, everything else is pretty much the same for set up between the two. You still have to get out and hook up utilities, unhook the toad or truck, etc. And the newer ones can have autolevelers, auto slides, auto awnings, auto toilet flush, etc. just like the motorhomes.
so go look at the floor plan you like, and go out and have fun, after 35 years you deserve it! I just started too late to get 35 years in before I was too old to do the young man's job any longer safely.