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.