As of January 2014, the ACA made it illegal to base premiums on current or past health status. So at least in the US pricing like this no longer occurs.
Which means that if your current and past health status are poor, you're probably aware of this, and should sign up for the best insurance you can, since you're far more likely to reap the benefits. You should overinsure yourself, and buy some investments in the hospitals that you're going to be visiting.
Those with above average current and past health status should enrol into the very least amount of insurance they can get away with.
This is, of course, why the law against changing premiums based on a person's health status was combined with a law requiring everybody to buy fairly comprehensive insurance whether or not they want it.
