Out of your questions: "Can you take a vacation any time you want?" is an interesting case. This depends on your career a lot, not just on net income. Some well-paid careers are notorious for being time-intensive and competitive to the threshold of burning out. You can take a long vacation, but your job might not be there when you return. I opted out of this rat race a long time ago.
"Something tells me that Harvard graduates "survive" any and all black swan events significantly better than many others."
Where I live, the Holocaust and the Communist coup were two notable exceptions. People who had a lot of property to lose often hesitated too long before GTFOut and found the way shut after rationalizing the first warning signs away.
It is possible that the USA is protected enough that something like this will never happen there.
