As I have heard...you only regret the things you haven't done....
IMO, the majority of answers will be of the opinion, to rent the house or at least keep it for a year. We didn't. Sold house, gave stuff to family yard sale for rest. Only had storage space for 3 months, waste of money to me. That was in 2004. Now, to be fair, we already had a rv site which we owned. We stayed on site, traveled when we wanted and spouse's health made it possible.
I did all the driving, whether motor home or towing a fifthwheel,most all the breaking down and setting up, he was not capable. He passed away last year, I have since taken 4 trips with just fur kid.
Have full time with 27' to 33' units. We/I, found about 30-31' to work for us.
No, do not plan to go back to S&B...I will be 73 shortly. Still have places to go, sights to see.
I use Passport America a lot, do not do the Wally world camping. Have done state parks and will do Corp of Engineers park to cut cost.
Your plan of truck and TH sound good to me. Yes, I am familiar with weights, all that stuff. Not an expert, but a good amount of knowledge.
Helps if you are a Mr Fixit for somethings. I will attempt minor stuff, no LP
or electrical problems. Just found a leak, did all required to fix it and watching it before finishing it off.
Health insurance is Medicare, we both had BCBS, which covered us in any state when things happened. For vets, I asked at the Campground.
Will help if wife knows knows how to do some "blue" jobs, not just the pink jobs.
? hook up and empty tanks, hook up water, hook up electric. If she will learn to tow, that would be a plus, for an emergency.
Good luck in whatever path you follow for retirement.
