The HIPAA continuous coverage and preexisting condition exclusion statutes apply to group coverage, not the individual market. There are states where either (i) individual health insurance is regulated as if it were group coverage or (ii) sole proprietors can obtain group plans. Illinois is a large, populous state where I believe neither of those are true.
I'm glad you were able to obtain coverage on the private market, but when I started my company in 2005, I tried to pay for it for my family and various members of my family were declined from every insurer in Illinois. I have had continuous health care coverage since 1994.
You made allusions to our "willingness to pay for the true cost of our coverage"† (my paraphrase) in our previous conversation, which I assure you has nothing to do with my complaint. We weren't charged extra (though an extra charge would have been unfair, I'd have paid it and gotten on with my life). We were refused any coverage.
The solution to this problem was to set up a group plan at Matasano, which we were able to do because (a) we're large relative to most YC companies and (b) we have a full-time finance/contracts person. That solution does nothing for whoever takes the job this thread is discussing.
† You also asked where the perceived belligerence in my last reply to you came from; implying that I'm complaining that I couldn't get a free lunch is where it came from. The implication is particularly irritating because my complaint isn't that the "food" (to torture the metaphor) was too expensive; it's that the sellers decided to starve us.