This first-person, insider narrative is hugely informative. I would summarize the major lesson in a single formula: Insurance = socialized economics.
The basic insurance model consists of lots of people paying a little so that a few people can receive a lot. Over time the insurance provider becomes an indispensable middleman who — in the case of health care — stands between the service provider and the patient. Thus, whereas service delivery once was accomplished with only one contract between two parties, now it requires two contracts among three parties. This doubling of complexity drives out free market transactions, leading to price escalation.
It would be good to eliminate the middleman. As the essay shows, eliminating the middleman also can be feasible.