Strange comment about Pittsburgh's diversity and strangeness! In my experience, outside Oakland, Shadyside, Squirrel Hill, perhaps Monroeville, and some working class neighborhoods, Pittsburgh is a fairly conservative South-US-ish city.
Bingo. The farther suburbs are fairly conservative, midwesternish in culture. Though the areas you mentioned (SqHill, Shadyside etc.) provide enough of a cool college-town vibe to perhaps be sufficient as a nucleus to attract (or rather, keep) the young college graduates required for general optimism... not just startups.