"Hard to break free of that system though...everybody expects the benefit, and it costs the company less to provide the benefit than they would have to pay you extra to afford your own insurance."
True. Right now, you do not pay income tax on the value of the employer-provided insurance that is provided by the employer (i.e. that which is not charged to you as premiums or deductibles - employers used to pick up most the tab, and still do pick up some of it). It was usually not even possible for you to get a good answer from HR on the value of that. In the past several years, something akin to the value of that untaxed benefit has started appearing on your W-2 (as information only - not included in your taxable income).
McCain floated a plan in the 2008 U.S. Presidential race to slowly phase out that untaxed-benefit, which would ultimately divorce health-insurance from being mostly employer-provided: it would start including the value of the employer-provided health insurance as taxable income to you, and then provide a tax credit that would cover the majority of this new taxable-income (based on some value of an average health-insurance plan). Over time, that credit would be reduced, under the theory that in a perfect free-market for labor, wages paid would adjust upwards to compensate as previously-health-care-providing employers competed on a tax-neutral playing field against employers that paid 100% in cash (whose employees would purchase their own insurance with after-tax money, just like any other consumer purchase).
This would help to disclose both how much health-insurance costs (theoretically bending the health-case cost curve down), as well as ramping down any tax benefit associated with employer-provided health insurance. Eventually, when there would be no advantage to employer-provided health insurance, people would buy policies on the open market without any connection to their employer, and you would be able to carry that policy with you when you changed employers - no COBRA, because it's not needed.
Of course, that plan did not address all of the other problems with the health insurance market, and of course not all of the problems with delivery of health care in the U.S.. But I liked the plan, because it provided a glide path that seemed to make sense, in reaching a goal of separating the purchase of health-insurance policies from the employer you happen to be working for at the time, when that connection no longer makes any sense.