Overall, Pittsburgh is a gloomy, depressing place to live thanks to its glum weather and sense of overall decline. On most days, you will find a gloomy, overcast sky overlooking rusty bridges, grimy roads and tired old buildings that have not been maintained since 1787.
It takes about three months or more to learn how to navigate the highly confusing road network, which appears to have been constructed crudely out of bits and pieces of streets built at random. It was apparently one of the first attempts to build a road network and so every possible mistake was made here.
Almost all roads are two lanes (one on each side) and so a single sluggish dumptruck can ruin your afternoon.
On the other hand, driving the winding roads can be a joy in any kind of sporty car because they are so challenging. Until you meet that dump truck, anyway. Strangely, again, most residents don't take advantage of the driving fun; most of them drive brand new pickups or rusted out old American cars.
People really do use "Pittsburghese", an ugly, ungrammatical dialect that has invented phrases like "The car needs fixed" and "Yinz". Yes, unlike some of the entries I have read, these really are used. I have heard them many, many times, unfortunately.
Even though the road network is horrible, public transport is worse, with an expensive and sluggish system. However, if you're a student or college faculty member, you can ride it for free.
A house that would sell in Los Angeles for $500,000 could be found in Pittsburgh for about $150,000. But don't be too cheerful about it; few homes in Pittsburgh are as nice to live in as even a humble Los Angeles tract home. Houses are badly designed to let as little light or view in as humanly possible. Most people close their curtains tightly against any sign of light and so artificial light is heavily used even during the day. This is thanks to a tight-knit social environment that features snoopy neighbors.
There are nice architectural details in many of the old houses, but unfortunately they are not designed with any sensitivity to light, the site or views. So you might have a magnificent hillside with tons of houses, but none of them take any advantage of views or natural beauty. For the most part, the only views will be of someone else's living room -- or, to be more precise, their living room blinds.
Real estate taxes are extremely high - in fact, that $500,000 house in LA will have significantly cheaper taxes than your $150,000 house in Pittsburgh. This and the cost of heating oil during the winter goes a long way to make those housing costs look much closer than you might think.
It may seem promising that the city is on the water, but it's a grimy, ugly waterfront that consists mainly of rusted-out steel mills and decaying industrial plants. Due to the frequent flooding and all that old creaky industry that was on the water, there's very little housing on the water or even with a view of the water.
If you have good personal relationships and connections, you can go far, and the business environment is relatively undemanding - even highly mediocre, if not downright awful stores and restaurants can thrive.
I was finally able to find a few decent restaurants, but most of best ones are the chains like Bravo and P F Chang's. I can highly recommend Pan Asia on Route 51, Cambod-ican on the Southside, and Thai me up, also on the Southside. Most of the other places I have tried have been terrible. Let's just say that this place is a poor restaurant town compared to pretty much anywhere else in the US and leave it at that.
For groceries, Giant Eagle's Market District is actually pretty nice, much to my surprise. Most Giant Eagles offer mediocre food at high prices, so I routinely make the lengthly trek to my closest Market District, where I can get better food at the same prices. There are a whopping two of these stores in the entire Pittsburgh urban area. There is one Whole Foods Market, close to Downtown Pittsburgh.
Otherwise, Giant Eagle is bad, Foodland is worse, and Wal*Mart pretty much rules by comparison. It's pretty darn sad to live in a place where Wal*Mart rules.
On the upside, this is a very honest place. If your car has a broken lock, and you have to leave your key in the ignition you need not fear; it will be there when you come back. I have left my laptop computer on a chair in the bookstore, only to see it there when I returned for it in a panic half an hour later.
Otherwise, I haven't found the people to be particularly impressive. This is a clannish town that feels suspicious of strangers. In fact, people often will stay in their native clan areas and not go elsewhere. There are many people who live in the South Side, for example, who will not visit the North Side or Downtown or anywhere else no matter what. The horrendous road network (see above) does not encourage exploration or leaving areas that you are comfortable with.
If you want people who are "honest" and "genuine", I suppose this isn't bad. But if you like people who are adventurous and love innovation and new things, you will not like it here at all. If you want people to seek out great places to eat or wonderful experiences, you'll find people here just don't care; they would rather go to the places they have been to hundreds of times before -- even if those places are abysmal in every way.
Most people here are sports fans. The Steelers are definitely an addiction here, since they are just about the only world-class institution the city has to offer. Even I, the #1 non-sports fan, have caught myself caring about whether the Steelers win just because so much of the city's mood depends on it.
So, in summary, a gloomy, depressing place that's losing population and gets just a little poorer and a little grimmer every day. A cheap cost of living doesn't help when you feel that your life is seeping out of you every passing day. Living here is empathetically not recommended, no matter how cheap it is.
Pittsburgh is one of the gloomiest cities in the UsA.