The way points of this running / walking route:
Amani Coffeehouse
Wood St Station. Catch the T to South Hills, or buses to Lawrenceville/Aspinwall, Strip/East End, and the occasional 100 to Oakland. Buses to South Hills, Hill District, North Side are nearby.
At 12th Street, you've gone just over 3 miles and are just starting to get into the interesting part of the South Side---the Works is another 15 blocks down Carson.