Since that time, things have been going well. One of willheim's suggestions was to reach out to alumni of my alma mater, and that one turned out to be the winner.

I felt strange at first, but I started sending emails and LinkedIn messages saying "I'm new to Philadelphia and I see you also graduated from my alma mater. Would you mind grabbing a cup of coffee with me, and maybe giving me a little bit of your local wisdom?"

I did this a ton of times, and wound up with three very positive outcomes:

1) I got a social life, which was emotionally fantastic.

2) One of my fellow alumni works in HR and they gave me great, honest feedback about my resume and some of the cover letters I'd written that (I believe) made it much easier for a hiring manager to understand what I bring to the table.

3) Another one of my fellow alumni tipped me off about an unadvertised position in their firm that's a great fit for me as a first step back into corporate life.

tldr; 127 days later I have a network of local friends and acquaintances, a great job, and my debt is shrinking at a $6k/month clip. And a large part of this is because I took willheim's advice about reaching out to alumni networks that (honestly) I never would've thought to tap.