I would argue having to fly to the coast is a problem, as is having an airport that is not a major transport hub with many direct flight options. I like to travel. And I'm not a big fan of the cold and gloom and it is cold there 5 months of the year. I believe Pittsburgh also has the fewest sunny days of any major US city. If it wasn't the least it was bottom 2. There are sunny day statistics available on some govt website that I reviewed.
I looked at a job there. It seemed like a good fit. The people were nice, they were totally gutting a place for a fancy new children's hospital, decent income potential and lifestyle, but the location was a deal breaker for me.
I love Pittsburgh for reasons mentioned elsewhere in this thread, but this post is entirely accurate. As GomerBlog advises, don't worry too much about the weather. It's going to be 72 degrees and fluorescent wherever you match. I'd recommend finding an apartment with an attached garage when you arrive so you don't have to shovel snow at butt-oclock in the morning.
The city tends to be more popular for those with families than those who are single and still swinging. Lifestyle is good.
UPMC was extensively discussed on here last year, so I won't go into great detail, but to respond to a few things:
The new Children's Hospital is here, everyone loves rotating through it (except the AGH residents).
The job market looks extremely tight here right now, odds are pretty good you'll have to move again after fellowship or residency. I wish someone had told me to think about this a little harder when I was looking at residencies.
There is no problem with regional numbers for anyone - I got them about two weeks into my first regional rotation. I'm unclear why we have this reputation since our regional program is strong.
You work a lot harder (and get scutted a decent bit more) than they make out on the interviews, but I suspect that is universally true.
I can't imagine I was ranked that highly here as I have no real connection, but I still matched
Yes, we rotate through a gajillion hospitals. It pissed me off last year - I think it's really hard when you don't have your feet firmly on the ground in the specialty itself, but I've gotten over it.
It's a big residency in all the classic ways.
We still have an interim department chair. We can't find a chair, which I think has a lot to do with UPMC +/- qualified people available +/- very high standards.
Like all residencies, some things suck and some things are great, and you have no real way of knowing about them unless you actually go there.