Nice analysis, i agree with you on most of your points. I don't remember if you have family or are you planning for yourself.Yes, I still think (Best combination of high quality of life, entrepreneurial freedom and low taxes) summarizes the options quite nicely.
Weather is quite important to me, so that excludes Switzerland and Portugal - even though if Switzerland was tropical and had nice beaches it'd definitely be number one.
At the same time the general goal of living in a highly developed, democratic, tropical and English-speaking country is still the same. These requirements rule out most of the world and what's left is basically USA, Australia and possibly Singapore / Malaysia.
I've spent longer periods of time in Australia and really like it. However, it is too far away from friends and family to be able to commit to it for the long-term at the moment.
I plan to visit Singapore / Malaysia (hopefully soon), but I expect it won't be my kind of bread.
That leaves the US, especially Florida. All in all I think it is the best option for me, but it will take a while to get a visa. On top of that Covid cases are currently exploding over there, so I am not that keen to move at the moment anyway.
This means for now I'll stay here in the Caribbean, work on my businesses and see how everything goes.
In this case maybe you can consider to live somewhere half of the year (for tax saving purposes) and travel somewhere else when it's cold.
Anyway i thought about moving to Florida or California as well so many times.
The second choice probably fit me better.
But the cost of living, hard time to get visas and high taxes froze me out from making the move.
Have you considered these things?
How much will be your tax rate and cost of living there? And what's your plan to get a visa?