Friendship gets my endorsement. Shadyside living for ~$300 less per month. Plus, if you decide to kick that pesky veganism, you're equidistant between Tessaro's and The Sharp Edge (mmm.....burgers).

There are a few other places I'd live in PGH (Lawrenceville, Strip District, etc.), but getting to Oakland on two human-powered wheels would require at least a Powerbar, if not severe blood doping.