Wow, another ecomodder form the 'burg I didn't even notice your location.
It is tough bike riding out that way and I have only ridden out thesre a few times. Have you checked out forum on
bikepgh.org ? The guys out there are great for route advice. I regularly commuted from highland park to etna. It was only 3.5 miles but mostly uphill on the way back (at least it make for an easy ride in the morning).