A group of independent contractors is maybe simpler to think about than YC and the companies it produces.
It may be that health care being tied to employment is the real problem. The customer of the insurance companies are corporations, not people. That leaves two options: become a corporation or create an alternative means to get health care.
For the startup crowd, becoming a corporation is the obvious path. Founders may go without health care during the early days, but the ones really out of luck are independent contractors.