I’d like to start by admitting that I’m not nearly qualified for anything I’m writing here to count as “definitive”. So take it with a huge grain of salt, do your own supplemental research, and don’t hold me accountable for any health, financial, or legal trouble you might get yourself into.
This is a strange post, and one that mostly targets the intersection between health insurance, financial strategy, and general risk/reward. It’s probably most useful to people who are pursuing financial independence / early retirement (FIRE), working on starting their own businesses, taking time off to travel and live on savings, or doing something else delightfully unusual.