So here are my takes.
1. If you ask on the class A forum, they will tell you the class A is the only way to go. If you ask on the TT forum, they will tell you the TT is the only way to go. If you ask on the TC forum, they will say to dump both and get a TC.
2. You have and are comfortable with the TT setup.
3. You are concerned about additional costs involved with the class A (setting up the jeep as a toad, recouping costs if you don't like it).
4. You have this one big tour of the U.S. in the near future and want it to be comfortable and happy for all of you.
5. You just bought the tow vehicle.
6. After owning a class C, you have gone on to own three TTs.
7. You are concerned about fuel stops with the TT.
8. Your usual trips are within 300-400 miles from home which has,been fine with the current setup.
With all that, it sounds like the only negative of your current setup are the fuel stops.
So, if you switch to the motorhome and hate it, you're going to take a loss. Either with selling the class A, setting up a toad, and/or buying a new tow vehicle and TT.
If you stay with your current setup, you know what you have. You won't miss what the class A might offer because you've never had it. However, you are likely to miss what you know with the trailer if you go to the class A.
So, I say stick with the TT and enjoy. You can deal with the fuel stops. You won't need to put any money out on a new setup right before your big trip. And you know the TT will work for all the trips after this.
