Big jump from tent to MH or 5th wheel. I'm doing much the same yet opted for a TT.
The choice is really personal and depends on how you want to live, the length of time you'd like to use it for ( F/T or weekend or extended but short term use) as well as the viability of a suitable TV in your life.
You already stated that a pickup is fine for you so I'd concentrate on figuring out which of the 2 styles you'd prefer.
As for ease of care.......guess it depends on how much knowledge or cash you've on hand for maintaining a mechanical system.