I'm actually not certain where this idea that all conservative bloggers get a corner office and a health insurance card comes from. You often hear that the right is way better picking up their young, but I don't really see it. So far as I can tell, the rightwing think tanks aren't actually stuffed with marginally-productive online hacks (just with normally productive, traditionally-hired hacks), Captain Ed doesn't have a sinecure anywhere, and Tigerhawk is still employed in a non-political capacity, etc. Some folks on the right do get jobs. Some folks on the left get jobs, also. If there are numbers showing this disparity, I'd like to see them, but I'm increasingly coming to believe that folks on both sides just think their party should do more to support its activists, and tend to project that strength onto the opposition.
That said, the core of the critique is right: It would have been much better if James Cappozolla had possessed health care. But his health care shouldn't be dependent on the largesse of liberal foundations, and thus his usefulness to the cause. He should just have health care. And then, if, in 2003, he had wanted to live on low freelance wages and put all his time into pushing this new "blog" thing forward, he would've been able to do so. We should free people to be as productive and occupationally independent as possible. The current system's bias towards working for well-capitalized employers in fully-matured industries is not only destructive to personal happiness, it's economically idiotic.