I'm going to bump this up and ask anyone in the area what they think about where they live and what might be some fantastic neighborhoods to apply Mustachian ideas toward a living situation.
My neighborhood as stated above is Mount Oliver Borough. For some odd reason I enjoy the fact that it is independent yet completely surrounded by the city of Pittsburgh. I don't think Mt. Oliver is perfect by any means, but I do think that it has potential. I'm a 5 minute walk from the business district with a library, a 5 minute walk from a park with some greenspace, basketball court, and playground, and a 10 or 15 minute walk from baseball fields, and much more greenspace. Plenty of good old housing stock (even though our house is about 50 years newer than most of the neighborhood). Cheap entry price under 75k for sure and more likely under 50k if you're willing to take something not recently renovated. Access to 4 different bus lines can take you to a wide variety of destinations if you need to get off the hilltop (or bike there and have the bus take you back up the hill). Close (but not too close) to the mayhem of South Side for fun diversions.
Negatives, housing prices lead to lots of renters, lots of Section 8 housing, etc. Not that these things are bad in and of themselves, but there is a modestly high crime rate. Also because of housing prices or lack thereof, there is a good chunk of vacant/abandoned housing that is occasionally torn down. I will freely admit that there were two homicides under a mile from my house in the last two months, although that seemed to be a random spike since for the year prior to that there was just one. I have never been a victim of any crime, and much of it seems to be drug related crime. The assigned schools are poor, though we do not yet have any kids.
In short, I like the neighborhood a lot, though we will likely consider moving in about 5 years, and holding this house as a rental. Unless there are quick movements that improve the neighborhood in that time.
A neighborhood that I'm interested in is Regent Square which includes portions of Wilkinsburg, Edgewood, and Swissvale. The proximity to Frick Park is fantastic. Much flatter terrain would make biking much easier and public transportation not as important (though I believe there is still at least one bus route through the neighborhood). The business district on Braddock is vibrant and interesting with a variety of retail and dining. I don't know much about the housing stock there, but I suspect it is similar to most of other Pittsburgh neighborhoods, older, a bargain by nationwide standards.
So let's hear what you think and (sorry for my overuse of parentheticals).