Hi! I am a resident of Pittsburgh and have been for all 21 years of my life, so let me tell you a little about the city.
Pittsburgh is very interesting in that it has so many different neighborhoods that were settled by different nationality groups. The Polish settled Polish Hill, Bloomfield is where a lot of Italians settled, Squirrel Hill is primarily Jewish, etc. So each of these little neighborhoods have a lot of ethnic flare.
Also, compared to other, bigger cities, Pittsburgh traffic is a breeze!
With Carnegie Mellon, Chatham College, Carlow College, Duquesne, and Pitt all within a few miles of each other, there are a lot of college students running around. There are always concerts or plays to go to if you are into those things. Apparently we were voted "#1 music scene in the nation" and another I think it is good, after being to other cities, I deifnately wouldn't say that. One of our most popular venues was just shut down last week, so who knows. We also have lot of cool art and museums, so if you need a break with studying, there are outlets.
Also, most people in Pittsburgh are some of the nicest people you will meet. Out-of-towner people often comment that you can ask anyone here for directions, and tey will gladly offer you some help =) So we are known for our niceness
Unfortunately, Pittsburgh has a lot of problems as well. For example, when the steel industry collapsed, there was nothing of that magnitude to replace it. Before my time, we were once a very prosperous city. Now, unless you are interested in Medicine, Education, or some banking, then Pittsburgh's job market is horrible. As a city in decline, crime rates have went up. One of my friend's apartments was just broken into and robbed last weekend and another friend was mugged two streets away from where I live. The Mayor here is horrible and doesn't knowhow to do anything except tax and spend. It's ridiculously expensive to park downtown now due to the recently increased parking tax.
Also, when I go to other cities, people are more tolerant. I am moving to California next year and everyone around here is like "Why would you want to move THERE?" "You know, there are GAYS there?" "Everyone there is crazy and LIBERAL" And it's just an old fashioned, closed-minded mentality that I need to get away from. PA is a rather conservative state.
Also, the transportation system stinks. Chicago, NYC have great systems. You come here and the busses don't usually run past 11 PM. No real subway system unless you are travelling to the south hills.
I used to ride my bike more, but as far as bike riding...well, I think we are the 9th most obese city in the US. There are, at most, only 90 clear days here a year, so it's not always easy to keep a routine. The car drivers here ABSOLUTELY HATE bike riders. One of my friends, who refuses to do anything except ride her bike, has been hit 9 times since we started college. There are a few good trails here ("The Jail Trail" that runs along the Monongahela River, and the Frick Park and Schenley park trails are nice too), but as far as riding on the street, be careful because cars do not care about you at all.
Lastly, I've noticed that places in other cities stay open much later than here in Pittsburgh. After about 9:30 PM, the only places left to go are bars and 24 hour diners.
I am sorry this was long, but I hope it helps! If you have any more questions, please ask. Overall, I love the city, but after 21 years, I gotta get out! =P