This doesn't have to be all or nothing. You could "retire overseas" and still spend part or even lots of your time back home.
I make the point in case it hadn't occurred to you already. The idea of moving to a new country, full stop, full time, can be intimidating. Selling your current home ... off-loading your car, your furniture, your lawn-care equipment ... flying off to a new country where you know no one and where everyone you meet speaks another language?
Boiled down like that, this retire-overseas agenda can seem foolish, even terrifying.
So don't sell your home. Keep your car if you like it. Lock the lawn mower in the garage. Pack a few bags and head off to someplace that's got your attention for, say, a month or two. Don't even think about buying a house or anything else. Rent small and modest. Or arrange an extended stay in a B&B or guesthouse.
Keep it low key and low pressure.
Because this doesn't have to be like jumping off a cliff. You can ease into the idea. Then, if you find the place you take for a test spin disappointing in some way, you can return home (remember, your car's waiting for you in the driveway) ... and begin planning your next "retire-overseas" holiday. Give someplace else a chance.
You could continue like this for years. You'd be enjoying some of the benefits of a new life in a new country (maybe a dramatically reduced cost of living ... definitely a richer quality of life ... better weather ... cheaper medical care ... new friends ... big adventures ... plus little luxuries you probably can't afford now -- full-time household help, for example), but you'd have a safety net.
What you'll find is that, with each retire-overseas foray, your confidence will build. And your plan will evolve.
Next step, maybe extend the length of each retire-overseas vacation. You could spend three or even up to six months at a time in each new place, depending on the jurisdiction's residency restrictions, thereby avoiding the visa issue.
You could begin renting out your place back home when you're not using it. This income would help to subsidize the expense of your retire-overseas wanderings.
You could, eventually, invest in new digs in a place you decide you like well enough to want to return to regularly. Again, rent out this apartment or beach house when you're elsewhere to further supplement your retirement income.
Maybe, eventually, you find you're ready to sell your place back home, because, as time passes, your connection there seems less and less important. More interesting are the new places you're discovering, the new friends you're making, the new adventures you're having.
Take it one step at a time and let your retire-overseas plan develop organically. Just as there's no one-size-fits-all overseas retirement haven, neither is there a retire-overseas plan that suits everyone. This idea is infinitely customizable.
One thing that has struck me over the three decades I've been covering this beat has been the diversity of situations among folks interested in taking off to launch a new life in a new country ...
One is looking for a place at the beach where he can spend two or three months at a time then return home to his wife who continues to work and isn't ready to make a move ...
Another is looking to build a portfolio of second homes to which he could escape now and then but that he could also count on to generate good yields over time ...
One is interested in snow-birding it in the tropics ... and another wants to clean-slate it, to sell everything she owns and start over, full time, someplace new and exciting.
Some are moving alone, single men, single women ...
Some are moving with children, with business interests, with friends, with pets, with container-loads of antique furniture ...
Big budgets and tiny ... immediate timelines for taking the leap and 5- or 10-year plans ...
Retirees, pre-retirees, entrepreneurs, and, most recently, digital nomads ...
Each agenda makes sense in context. And none might make sense for you ... meaning you should invent your own.
My point is that you don't need to make any long-term, all-or-nothing plan before you set out.
Keep it simple. Take a trip.