As a native of Pittsburgh, I feel that I have to go to bat for my hometown. Pitt gets a bad rap for weather and overall dreariness. The people that perpetuate these ideas are those who think that Pittsburgh is a decrepit steel mill-infested town ready to die or those whose only knowledge of Pittsburgh comes from friends of friends of friends. The reality is that not one steel mill or large plant of any kind remains in the downtown vicinity, save for a cement processing plant and a few warehouses here and there. Most of the city's riverfront has been transformed in recent years to tech industry headquarters, mixed use retail areas, housing, and parkland. Sure, the old industry towns that line the rivers outside of the city continue to struggle and are not pretty to look at, but the trend of revitalization in the region is certainly growing. And the truth is that you will hardly ever find youself in one of these run-down towns unless, 1) you are assigned to UPMC Braddock or another satellite for a rotation, 2) you are hopelessly lost, or 3) you are grossly misguided and can't find a place to live in Squirrel Hill, Shadyside, or Oakland (the neighborhoods surrounding the Pitt campus).
It is true that clouds often descend on the Pittsburgh metropolitan area. But the talk in recent message boards about the negativite weather in Pittsburgh suggest that Pittsburghers are trapped in a dark, monsoon-like state. A more appropriate description of Pittsburgh weather is overcast; the sky may be subject to cloud coverage, but this state is transient and plenty of sun makes its way to the ground level. The biggest drawback of the weather is the humidity in the summer. There isn't a particularly large amount of rain in the Burgh; when it rains, it pours, but you don't often see persistent, annoying rain showers that other East Coast cities experience.
Regarding city life, I have been hard pressed to find neighborhoods as pleasant as Shadyside, Squirrel Hill, and Oakland. I have lived in Boston and New York in recent years, and I have not come across a place that combines quality of housing, affordability, safety, amenities, etc. as well as the aforementioned neighborhoods. You can live inexpensively in Pittsburgh and live well. Parking permits are easy to obtain in city neighborhoods, and there is ample on-street parking except in the immediate area around Pitt's campus. Squirrel Hill is a largely Jewish area with nice houses, parks, and lively shopping district. Shadyside is a younger area filled with restaurants, boutiques, and trendy shops. Oakland is a very diverse area, not as polished, home to countless Pitt students as well as old-school folks who have lived there forever. There are no shortages of social opportunities, and you can bet that going out on the town will be much much cheaper in Pittsburgh than in most other cities. The person who discussed the prevalence of $1 beers knows what's up. The only bad thing about the social scene is that Pittsburgh is behind the times with anti-smoking legislation; plan to come home from the bars smelling like a cigarette, unfortunately. Finally, one of my favorite aspects of the city is abundance of green space. Frick Park and Schenley Park are incredible, bottom line. Pittsburgh has one of the best urban park systems in the country when you consider miles of trails, acreage, and quality/maintenance.
Since I am not a medical student at Pittsburgh (although I may be next year), I cannot give a meaningful position on the quality of life/academics at the school. However, I have family members/friends who are part the medical community at Pitt, and I have done research at Pitt, so I can attest to the fact that Pitt is a first class institution. I think a lot of criticism of the Pitt system is that UPMC is a giant, powerful corporation in Western PA. A lot of what is good for UPMC isn't great for the Western PA economy since they are tax-exempt. In a business sense, there are some tensions in the region as a result. Setting these issues aside, the opportunities Pitt provides for students, employees, and faculty are limitless. They enjoy tremendous funding for medical pursuits, and they seem to put this cash to good use. The recent construction of several medical buildings in Oakland and a huge new Children's hospital in Bloomfield support this sentiment.
From my experience, the people at Pitt are good representatives of the region. They are friendly, driven, and proud of their institution. Pittsburgh is definitely not a fast-paced town, and because of that I think the school attracts people who are chill and more laid-back. However, the resources are in place to make the most of your experience.
In college a lot of my friends made fun of me for having Pittsburgh pride. They joked that Pittsburghers love the Steelers/other sports teams so much because they are the only things worth holding onto in the city. Few took me seriously when I described my [city] neighborhood, Squirrel Hill, and its parks, its golf course overlooking the city skyline, its pretty houses with spacious backyards, and its good restaurants/shops. Those who visited me at various points throughout college quickly changed their tune. It's easy to knock a city when the only thing you know about is that it used to be a steel town. It's also easy to refute claims of progression and development in the region when you haven't actually seen said progression or development. Pittsburgh isn't on par with big American cities like NYC, Boston, or Chicago, but it more than holds its own.
To address the initial topic, I think at any school you'll find people who are quick to defend their choice and sing praises about their school. Also, don't overlook the fact that a lot of the Pitt versus XYZ threads are between two of the best schools in the country; who wouldn't be hard-pressed to make a decision? Who knows though, maybe I'm just a low self esteem-having a$$hole who cannot think of anything better in the world to do than defend Pittsburgh on an internet forum. Just my two (very long) cents.