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[quote=Anonymous]In way, focusing too much on the city is a red herring because none of them are Portland, Seattle or Austin, or Denver, which attract enough similar minded people to give the cities a dominant personality that makes it attractive to others and justifies moving there (beyond jobs). It's all about finding the right group of like minded people and organizing your life around those people and your preferred lifestyle. All three cities would work out just fine for most people as long as they managed to do that. After all, how much of a difference is there really between Shady Side/Squirrel Hill in Pittsburgh and Roland Park/Homeland in Baltimore and Chestnut Hill in Philadelphia? I know that I would have the same lifestyle in all three cities and be perfectly happy.

I will put forward my own observations on the advantages (and disadvantages) of the three cities:

Pittsburgh:
1. Cheapest of the three, although the nice areas are still expensive, but par for par compared to other two cities you're likely to fare better on the real estate end. Lots of great and affordable architecture. 
2. Smallest city and metro area of the three, but still large enough to have the amenities of a city, with the supermarkets, shops and restaurants you need. Carnegie Mellon and Pitt ensure a sizeable presence of educated professionals in the area. Some good museums and cultural venues. 
3. Easy access to the hills and mountains of western Pennsylvania and West Virginia. Hiking, white water rafting, all easily doable. 
4. Lots of gentrification and renovation in the downtown area and along the rivers.

Downsides: geographically the most isolated. It's a long drive to the next big city and there's very little in between other than rural America and small, often dying, towns. There's a stronger "rural" and hill folk presence in the metro area. DC snobs might not like this. Urban schools are hit or miss. Pittsburgh is also very hilly, which not everyone likes or appreciates. There's no beltway around Pittsburgh because there are too many hills.

Baltimore:
1. Much cheaper than DC and slightly cheaper than Philly. Some great neighborhoods in the north side of the city (Roland Park). Great waterfront area. Good suburbs. Lovely architecture in the nice parts of town. 
2. Midsize city that brings pretty decent cultural scene with it, two large museums, a good symphony, and of course, only a hour from DC with all its cultural resources. Hopkins/UMD crowd ensures plenty of educated professionals, who congregate mostly in North Baltimore or around the waterfront (and the burbs). Plenty of good restaurants and supermarkets. 
3. Easy to get to DC and New York via train or car. BWI airport is easy in, easy out, although you'll still travel to Dulles for most international fights or rely on connections. 
4. If you love sailing, Baltimore is the city to be.

Downsides: it's a problematic city. We know this. Crime/drugs is a persistent problem outside the central corridor / waterfront and occasionally it spills over. Schools within the city are very much a miss with a few exceptions. A lot of decay in Baltimore outside the central corridor. And it's not going anywhere any time soon.

Philadelphia:
1. Cheaper than DC. Lots of great housing stock much more affordable than comparables in DC. Lots of gentrification both in West Philadelphia near Penn and north/south of Center City. The Mainline is a fabulous area to live, if you can afford it. Chestnut Hill is great. 
2. Much bigger urban area than both Baltimore and Pittsburgh, giving it a taste of New York. Wonderful Center City that is thriving. Excellent cultural scene, excellent museums, opera, symphony. Penn and the other universities add a young presence to the urban Center City environment as well as educated professionals. The best public transportation of the three cities with its subway and trams and regional rail. The old history of Philadelphia is undeniable. 
3. Handy for NYC. Some really lovely countryside north and west of the city, although suburban sprawl is persistent. 
4. Probably the best public schools of the three cities (within the urban city areas). Most of Philadelphia's schools are a miss, but there are some strong options and Masterman is the best public high school in the entire region. Suburban schools are by townships and are like any metro area, rich areas have the best schools, poorer suburbs have the worse schools.

Downsides: it has all the problems of Baltimore, albeit spread out across a larger area and diluted by a larger population. There's still lots of problematic urban areas and poor schools and obtuse city government. And it is weirdly dirtier than you'd expect. A lot of litter, unfortunately, especially outside Center City.

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