It is odd to me how he keeps describing his $500/month insurance as being useless: he is generally in excellent health and his yearly expenditures are low enough that he is always paying down the deductible. Does he feel car insurance and home insurance are useless since he didn't total his car last year and his house didn't burn down? He knows this (as he mentions it obliquely) that he could lower his deductible but…
Imagine a regular sized family of 4, you have to shell out more than $20K/year for the most basic health insurance for your family if you are self employed, $20,000! and you still have to pay for EVERY doctor visit for your kids and regular checkups, and your family deductible is around $10-12K. And every year they send you a new increased quote by 10-15%. There should be some kind of a discount for families, like wh…
Even so, a $20k a year is peanuts compared to the out-of-pocket expenses of a serious medical emergency. Don’t fall into the trap of thinking insurance is not with it just because you haven’t had to use it yet.