Greenfield's alright. I've lived there about 10 years.

Pros: Close to everything, walkable (if you like to walk) to places like Oakland, Squirrel Hill, Frick Park, Schenley Park, and even Shadyside and beyond (about 35 minutes to Walnut St, if you hustle), and all the dining and shopping opportunities that entails. More affordable than those neighborhoods, and your mortgage may end up being significantly cheaper than what it'd cost to rent in Greenfield, though the cost of the average starter home around here is already up around 100K from when were were buying a decade ago (now most of the cheaper homes are in the 225 - 270K range for a basic 3BR/1BA place, with it going up if there's any sign of recent remodeling). Many of the homes at least have a small yard, which is good for a dog and a garden. Regular bus service to Oakland, Downtown, and the Waterfront. People are generally friendly if/when you get kids into school, and I've generally been pleased with the school communities and opportunities on the sports teams and at the Rec Center. Really great views from some of the hilltops. Lots of wildlife, which is fun to watch but bad news for our plants.

Cons: A lot of the homes are really old and suffer from remuddling and deferred maintenance, as I've been discovering (purchased after a series of owners who only stayed there for a year or two), which has meant a ton of extra work on things like roofs, chimneys, heating, insulation, etc., plus any decorative changes. Drivers are really shitty because it's a cut-through neighborhood, so people who don't actually live here end up running stop signs and red lights all the time. Then again, the people who live here also speed and ignore signs as well. The Nextdoor is toxic, but that seems the same everywhere.