Health insurance costs vary dramatically. My wife and I have bought our own insurance in CO, CA, and OR. We usually pay around $150-250 / month (for us both, not each) for a decent plan with a deductible of $2k-5k. I always use esurance.com.

That said, he's in the worst insurance market in the US: NYC. To get the equivalent of the $168 / month plan we have now, esurance was at least $800-1200. Sickening. Best bet I found is Freelancers Union. Health insurance is horribly broken in NYC.