I, too, was in the same situation, about 6 years ago (and am finally seeing the light at the end of the debt tunnel). My numbers were spookily similar, too. 4+ years of not working, having to eat, buy books... they add up, even when you are trying to be careful.

I empathize with how hard it is to get that first job. It took me a while. Lots of resumes got dropped into a black hole.

What I did:
I moved back home for a year (not the most fun), and did some bartending. (Hint: having an evening job made it easier to conduct the job search during business hours).

When I moved back out, I found a place two blocks from my job. I was able to get by w/o a car, which saved me a *lot* of money.

And, I skipped the health insurance. I understand both sides of this (you are taking a risk, and if you have ongoing health concerns this may not even be an option). I was lucky, and did not need it.

As for the job search... talk to your friends. All of them. Find out what they are doing, how they are going about it. I took my first "real" job at very low paying association to get the experience. Six months later, I actually started getting responses to my resume when I went looking again...

I hope some of this helps.
-brad