I could absolutely see that becoming more of an issue for more people if the next step in profiteering is to have more contractors who do work for companies while having to get their own health insurance for themselves.

Also, the other problem with risk pools for healthcare in the US is that the most expensive risks - chronic illnesses like heart disease and cancer - are arguably the ones that no one wants to manage the risk of financially. Could you reduce those risks over time by making it more expensive to be obese, like we do with tobacco consumption? Probably, but it'd be incredibly unpopular with the insured.