> If you aren't willing to sue over a disputed liability, it might as well not exist.

I think this might be at the heart of it.

The article (about how hard actuarial math is) and the insurance buyers make the mistake of thinking that all that matters is downside in case of event X with particular probability P. However, instead you have to think about chances of X AND chances of being able to navigate a system that is outright adversarial to parties that are not the insurance companies.

The “house” always wins…