i have a few old friends who are doing the nomadic lifestyle and seem to adore it. in all cases they sold their existing homes and are traveling to their hearts desires. in all cases though, they did through advice or experience decide that they needed some kind of 'home base'. with at least one it was due to the realization that for tax advantages they wanted to establish legal residency in a friendlier state than they were retiring from, with some others it was to establish a primary care provider they could at least have call in regular scrips/sched to see for annual checkups. whatever works for folks-i just like seeing the photos they post of their adventures!
Yes, we have homework to do on this front...establishing residency somewhere when we sell the house...etc. I believe it's also a big deal where we purchase our health insurance on the ACA exchange as that will determine price, docs, out of network considerations...etc. I know that in the RV community a lot of people establish residency in South Dakota...you only need to be there 24 hours and there are services that forward your mail...etc. But healthcare is a concern. So...not sure there's any perfect solution.
I'm definitely not opposed to maintaining a reasonable apartment somewhere as a base...and nomading from there. We've gone back and forth on keeping the house, possibly renting it out, but have decided against that. It's too much of a pain and we'd be lousy landlords....too forgiving I think. Maybe being gone for 3 month stints...back for a couple in an apartment in another state... and out again would work. The other consideration early on will be our little dog, who is not a traveler to date, and from what I read the airlines are really curtailing the "in cabin" pets (not service or emotional support dogs)...even if they can fit under the seat in a carrier, etc. I've read about dogs being put on a "no-fly list" without explanation to the owners...lol.