To add to your tail risk point - I wonder how many people foresaw the Venezuelan oil crisis way back when, or even less likely, the Saudi Arabian oil complex attack in 2019. And of course, the current situation we're in with CoVID that an entire university of forward thoughtful looking people didn't call until it was a week away. As an aside, do insurance companies significantly alter their policies when such a cat-5 hurricane is imminent? What preparations would they make in the face of that sort of event?
Are you talking about chaos theory in the last paragraph? I'll read that article you linked in a bit and see what more I have to say, from skimming through it looks as though my question from the previous paragraph may be answered.