going from Class A to TT or Fifth wheel

With the same bells and whistles, it will take about the same amount of time and effort to set up. Now if you compare a loaded DP to a bare bones TT, sure it will seem spartan and more effort but that's not comparing apples to apples.

Particularly for a 5th wheel, driving is very comfortable...and even a properly set up TT isn't difficult.

What truck will you be using to pull a trailer?

In the pure traveling sense until recently we owned both our MH and a 33' TT. The TT was well set up and I pulled it with a '16 Super Duty diesel, 4 door long box, Lariat Ultimate package - the point being it's a nice truck and the right tool for the job.

With that said, I would rather drive the MH cross country than I would pull the TT across town. I just find pulling anything adds a level of stress not seen driving the MH. The one (*) I'd say is pulling the toad doesn't add much, if any, stress. The MH is big enough the toad is like it isn't even there.

Put another way, the TT is gone, the MH stayed.

As always, do whats best for you.

We moved from a 5th to a Class A 3 years ago. As we age we prefer the A for ease of setup and backing. Just push a lot of buttons for setup, rarely need blocks. Very nice when raining, windy or cold. The negatives for us were: less exterior storage, can't back up with the toad attached, harder to level if needing blocks and need to take the MH to get propane(have realy big tank though). Trailer and 5th are on a fulcrum so if not level they are easier to level and a 5th has a lot more basement storage.

All in all it is a personal choice.