alt Hacker NewsOr it becomes standardized to have exclusions - pilots for example often have extensive insurance that covers the company when they’re flying for hire, but covers nothing if puttering around in a Cessna on the weekend.
Insurance companies are very, very good at figuring out how to identify and price risk, once motivated to do so.
Sure as you'd expect lawyers are better at cutting a good deal for themselves than other professions, but I wanted to cite an example where it does work out.
Also from what I've seen there are way too many GA accidents involving airline pilots for the insurers to eat that loss. They almost invariably have superior skills, but some of them more than compensate with risk taking.