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I know several Americans who live in Panama almost full-time as "partially retired." They are successful, independent types who only speak English, want a stable place (in both politics, currency and property rights), and have a lot of $$$ they don't want taxed to oblivion. I think Panama fulfills most of your requirements.
Me? I'd prefer retirement to Alaska, Iceland, or somewhere in the Alps. Cold is good.
My plan is to purchase a sailboat (Catamaran) and actually live on the boat for a bit while deciding on a permanent island based home (hopefully with a dock yet high enough to avoid a hurricane tidal surge.
There are back issues of Caribbean Travel floating around the net and I would recommend them as a source.
Taxes seem to be the big issue unless you become a citizen of the country but one solution may be to form a corporation or LLC and funnel some of your income into the company. You could control the income in a trading LLC so that the profit would be 'reasonable' but mostly eaten up by expenses of the company.
If setup correctly, you can 'write-off' expenses of the company.
i.e. travel to and from the business and/or living expenses for travel to a company branch location.
(perhaps on the island of your residence).
As the CEO of the company your expenses to travel to 'training' locations (Caribbean Island) or other locations to 'research' investment opportunities would be deductible.
At your age, I would setup a trading account to trade in a Roth IRA.
The profit from trading would grow tax free.
Your day to day living expenses could be mostly covered by the 'expenses' paid by your company for them having you in a satellite location as a trading specialist. Your income (and taxes) could be controlled by how well you trade your company account.
(when the income is too much for the expenses, then your trading could go through a drawdown period)
FWIW
Rejoice in the Thunderstorms of Life . . .
Knowing it's not about Clouds or Wind. . .
But Learning to Dance in the Rain ! ! !
I skimmed over this idea a while back and came to the conclusion that Aruba or Curacao might be nice. Kingdom of the Netherlands Caribbean countries (formerly Netherlands Antilles), both outside the "Hurricane Belt".
One of my primary requirements is a high standard of living and decent local education. Beware of some destinations which only have nice resorts and the rest of the country lives poorly. I don't see that very appealing.
But as a more likely alternative to living out of the country, I'll probably do what a lot of people unknowingly do and that is disconnect myself from the media/politics and live in my own "bubble of a world" as I call it. The electorate is just down right gullible and the political games capitalizing on their naivety aren't going away anytime soon.
EDIT: Outside of the Caribbean, towards Asia, Singapore looks like an interesting place to visit.
Unless one is relocating for tax-purposes, I much prefer Hawaii to the Caribbean. Maybe even some quiet places on Australia's East Coast. But I must admit that I am a sucker for infrastructure...
Platform: "I trade, therefore, I AM!"; Theme Song: "Atomic Dog!"
Trading: EMD, 6J, ZB
Posts: 795 since Oct 2009
They are outside the normal belt, however, they share and benefit or are harmed from the weather patterns coming off the top of South America (but what do I know).
I do know, that whenever there's bad weather for a prolonged period of time (read hurricane or other weather pattern) the waters become turbulent and stir up all the ocean garbage that was dumped offshore a few miles away, and return it to shore as well as the beaches.
didn't see the mention of "Island Fever" or "Rock Fever" but it could be a real concern. Lived in South Africa for over 3 years when I was single, then later moved to Guam after a 6 year stint in Phoenix. If you like driving as a past-time, or just to see what's around the next corner or over the next hill, your curiosity will begin waning after a couple years. We learned how to scuba and enjoyed exploring/beach-combing, etc. and worked over 70 hours/week so were able to last about 3 1/2 years. Military families seemed to move every couple years so I imagine it wasn't too big a problem in most cases.