Recent developments have increased my interest in this topic. I am interested in education systems, medical systems, crime rates... normal standard of living concerns.

On the subject of health care, it of course depends on where you're moving. But for many destinations you may not qualify for local health coverage. Some places make distinctions among visitors, residents with temporary visas, residents with permanent visas, and citizens.

If not, there two main firms I know of which specialize in health insurance coverage for expats, being Expacare and Bupa. You want Bupa, not Expacare. You get to choose which sections of the world you're covered for. Unsurprisingly the big determinant of price is whether you want it to include coverage while visiting the US.

In the UK, to oversimplify a bit, any human in need is covered without charge, visitor or resident.

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Diversifying investments outside the US is not hard. My favourite is to have an account at Interactive Brokers and just buy stocks listed on exchanges outside the US, and/or convert your cash from US dollars to others. I am not a big fan of funds.

For any stock, the biggest thing that matters to currency exposure is where they make their revenues, not where they are listed or incorporated. The currency the price is quoted in is totally irrelevant. A distant secondary concern is the currency of their expense profile. e.g., a US electronics retailer selling goods produced primarily in Asia is essentially a bullish call on the US dollar.

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In terms of destinations, one of the first things I suggest people look into is whether you have a grandparent born somewhere else (or even further back in the case of Italy, probably soon to be cancelled). In a lot of countries the family tree gives you a much accelerated method of obtaining residence or citizenship. Plus, if you ever chose to renounce US citizenship and the tax hassle that goes with it, that process is very much easier if your apparent reason for doing so was ancestry rather than tax dodging.
e.g., I had a grandfather born in the UK, so I would have the right to live and work there. After not too long, that would give me the right to apply for citizenship.

Jim