Yes, but difficult to do accurately.
As for insurance, companies do try to assess risk. For example:
- my residential insurer checked distance to fire hydrants
- I have many examples of insurers being smart about assessing risk
But new pilots often crash because they are not familiar with basics lie avoiding stalling in turns. Similarly new automobile drivers lack knowledge and are often unsafe - three promising teenagers hit a tree in Surrey BC last wee, excessive speed was a factor. A problem is how to separate the well trained and careful from the riffraff, like the sports star who didn’t pull his little amphibian up soon enough - stunting and worse.