I have always felt like Americans living abroad have a small advantage because they have access to the lowest cost financial markets and there is an advantage in having a lot of your wealth by default in the world's main reserve currency -- its value tends to be anti-correlated with stock prices (IOW, my dollar is worth more abroad when world markets are down as that tends to help the dollar, dollar worth less when markets are up and there is lots of confidence but then I am rich anyway, this reduces the tails of the distribution).
My weighted expense ratio for my investments is about 0.2%. And because I invest in the USA markets, I can invest in worldwide assets with an amazing amount of diversification at such low cost.
Now, let's say that your move increases the costs of your investments (pre-tax) from 0.2% to 0.7%. Let's also say that you are doing a 3.0% SWR and that 5% of your expenses are due to having to live an itinerant lifestyle to maintain tax-free status (temporary housing, extra plane flights, admin costs, this doesn't even include the hassle factor).
In the case I have outlined, the pre-tax cost of paying 0.5% extra annual investment expenses plus 5% of your 3.0% SWR is .65% per year of your net worth. That is a 21.67% "tax" even though you are not paying any income or capital gains taxes to a government. Even if you are paying a 30% marginal rate, your total tax may not amount to 21.67%.
Also, if you are going to invest in real estate in a tax haven as your primary investment, your investments are not diversified. And the pre-tax return on capital will not be as high in a place like that simply because tax costs are lower (only the post-tax return on capital should be higher -- the rest of the benefit goes to increasing standard of living of people living there, not to capital).
I would do this sort of analysis in your case.
Also, it really is not safe to live in the USA without some sort of health insurance. With lots of cash (as you will have), you could probably do it relatively safely in any other country of the world, though. But you will get burned in the USA.