I don't think this knowledge is obscure. "Sky sports" are one of the few things that make a person practically uninsurable, along with scuba diving, motorcycle racing, and private aviation.
I don't know about motorcycle racing, but scuba and private aviation are plenty insurable. $1M 20 year term life goes for ~$100/mo if you're a younger pilot. There will be a somewhat smaller set of insurers to choose from, and a couple of outliers who try to charge you way more.
What insurers don't like is someone who throws off their "books" unexpectedly.
Not to be a shill, but I always use World Nomads Travel Insurance when I travel for scuba diving. It is simple to apply online and pay with a credit card. They have two levels of travel insurance: one for low risk activities, and another for higher risk activities, such as scuba diving.