> I'm trying to understand how what you're suggesting

Nothing. It's definition of insurance - selling your risk.

> Are you saying that we should only pool risk between people in the same risk bucket?

I mean, why would people want to be in a bucket with people with higher risk?

> How do you aim to determine the resolution of that risk? Not to mention calculating it accurately?

These are the problems of insurance companies. At the end of the day, the consumer simply chooses the best price for his risk.