"...but YC moved our time line up by at least six months to a year..." - can you explain further - in broad terms of course - was that because of the focus of the YC process; the connections being a YC funded company brought, or something else?
What's really hard for many founders (myself very much included) is telling your friends and family you're leaving this good job with health care benefits to do a startup. Having a name behind you makes this a lot easier; the YC money was almost irrelevant.
I can't think of any other benefit I'm missing. It seems to give a warm and fuzzy sense of security to a lot of people.
COBRA is a pretty bad deal though. Mine was almost $250. You can get a good Blue Cross plan for that much, or a simple disaster plan for much less.
What's a disaster plan? Google was not too helpful. It sounds like what I'd want.