As a 'name' at Lloyds (which is a market, not an insurer btw) the only risk assessment I do is choosing which syndicates to back with my risk capital. I'm not involved in the risk assessment part of risking my capital on individual insured risks. Those assessments are made by the man in the booth who actually writes the insurance. As a name I have two barriers of agency (Member's Agent and Managing Agent) between me and the writing of the risk.
In general, an insurer will look at the probability that an insured pilot will do something bloody silly. A pilot who has done something bloody silly may or may not do something bloody silly again, but such a pilot who does something bloody silly again is clearly at a greatly elevated risk of doing it again and again. Amelia Earhart is a classic example of that. She was a low to average pilot and a crap navigator, with a history of multiple pilot-induced accidents.
Almost any risk is insurable, if you have a backer with enough dosh pay the premium or underwrite the risk. Crash Tracey seems to have enough well-heeled admirers to financially enable her to go on to her next crash. Good luck to her and to them!