If you were moving sight unseen to an expensive city with a teeny tiny baby and hardly any money, what would you do? Besides worry. I'm already doing that 24/7. Here's what else I'm doing:

-Searching Craigslist to find the cheapest, non-scammy apartments
-Using Google Maps to figure out where approximately the apartments are and checking out the street view of the neighborhood
-Searching for grocery stores in the area, aiming for a variety of cheap/crunchy
-Checking to see if Matt could bike to school instead of spending $35/week on the metro

What else should I look for? I think it would be nice to be near a library. That is some free entertainment.

I found a couple cute looking apartments for under $1000/month (a STEAL in this particular city,) within a few miles of the university, near a park, with an Aldi and a crunchy co-op in the neighborhood. The walk score is not great, but I don't expect to be able to walk to the grocery store with a baby anywhere that we can afford to live.