On your third question, it is easy:

Get your passive income up to 2 times your families current expenditure. You will save at a rate much higher than inflation and it will handle even your extreme kiasu syndrome.

After a while, if your passive income is high enough, even education bills like $100K/yr for a couple of kids won't faze you.

If you have to spend $1m a year on hospital bills for 5 years, it's probably not worth living, so healthcare isn't an issue.

BTW, this what I think:
You will be able to travel first class until you are sick of it.
You will be able to buy the full carbon bike with $10,000 carbon wheels
Your age will make it frustrating trying to learn anything. Dementia, Alzheimers.
You will be able to buy a top restaurant and have the chef cook for you at home.
If your investments earn twice your expenditure, why fix something which isn't broken. If you get demented, you might screw up an lose it all. Just leave it.
From the way you write currently, I wouldn't try writing