Tangent: COBRA is a really bad idea too. First, COBRA is probably more expensive than health care you acquire yourself, because most employers acquire highest-common-denominator coverage and hide the expense in payroll and benefits accounting. Second, COBRA has a ticking time limit on it, which is exactly what you don't want with health insurance (and why you never want month-to-month or temporary coverage). You might as well not insure yourself if any catastrophic event is as likely to bankrupt you with insurance as without it, which is what happens when something bad happens in the latter part of your COBRA term.

I have a high-deductible plan from Assurant, with prices roughly equal to what they quote here (low $100s): http://www.assuranthealth.com/corp/ah/healthplans/individual...

Mandated insurance with guaranteed-issue is a tax on the young and healthy to subsidize the old and sick. My plan, for example, is illegal in NY and NJ which have strong community rating requirements.

You can certainly think that taxing single 20somethings to subsidize families and the elderly is a good decision as a matter of policy, but it's not going to do a whole lot to increase entrepreneurship.