HK is totally fine for LGBTQ, although china threat is looming indeed

If your concern is visa I think Thailand should fit the bill.

Most developed countries are out of the options since most of them have tight immigration, and since you are not working you are not going to be building permanent residency.

I believe you are at a very odd spot, you are rich enough to retire early but not rich enough to buy residency. Let’s say in Singapore you can actually have a residency if you have a family office but that requires like 200 millions. I don’t think you are at that bracket, but if you are, go for it, Singapore is a great home base to travel within Asia and it is pretty darn safe and well-managed.

Unless you by any chance was diagnosed with late stage cancer and need emergency treatment or maybe hit your head and went into comma, you won’t actually reach that amount (typically coverage is “reset” every year).

Even if you are hospitalised in most countries you will only spend a fraction what you could have spent in the US. Exorbitant medical cost is american specific problem.

I need a starting point

Marry a local.

PR requires residency which can come in the form of local job or study and you have neither of those.

Since when DN is tax free

The Singapore number is wrong. That’s way too far from median income, however maybe true if you are a nomad since legally SG doesn’t allow short term rental so you need to resort to hotels alike which can cost ballpark 3k ish USD per month

For expat the more “accurate” number is around 2.5k USD. Cost of living actually is lower in Singapore than in the States or Western Europe. You can live a good life with good QoL at 1k USD for food and entertainment as long as you don’t spend too much on booze or cigs.

Why don’t you ask about it in italy subreddit. This has little correlation with digital nomading.