I'm kinda wondering if YCombinator or one of the other incubators could do something like that. For me, a major reason why I'm not doing a startup now is that I'm not sure I could get health insurance. My last startup was done in Massachusetts when I was 25, so it was no problem to get an individual high-deductible policy. I'm not sure I could do the same thing in California, now that I'm pushing 30.