I'm from Lancaster County originally and moved to Philly in 2002. I've seen this city change at a rapid pace, some for better, some for worse. I'm a hotel concierge and a parttime tour guide of the historic district, so I get to meet a lot of nice visitors and I make sure they leave our town very impressed.
There's no denying Philadelphia is a national punchline, but that's for people who haven't visited since the 80's. Today you will find a major cosmopolitan feeling in our fair city.
The people can be awful. I mean, AWFUL. Especially the residents who've lived here their whole lives. But once you break through that tough veneer of "Broad Street Bullys," you will find lifelong loyal friends.
And you can't pick a better geographic center. To go out home to beautiful Lancaster Country, the most beautiful countryside on earth, hop on Amtrak for an hour from 30th Street Station. New York is incredibly easy and accessible multiple ways, by bolt/megabus for dirt cheap or by Amtrak to travel in luxury. Washington and Baltimore are fun for weekend trips. History buffs (like me) love our unparalleled place in American history right here, and Gettysburg and Valley Forge are not far trips.
My commute to work is 20 minutes door-to-door and I'm on the subway for 3 minutes.
Shopping in Center City - now that's kind of a bummer. We have GREAT independent boutiques in Old City, Midtown Village and Antiques Row. Walnut Street is our shopping strip in Rittenhouse, but all the high end luxury stores have been vacuumed up King of Prussia Mall, the largest retail mall in the world, which is a fucking pain in the ass to get to without a car. No train to KOP - they want to keep the Philadelphia riff raff out.
Art is ubiquitous around the town. Isaiah Zagar keeps South Philly beautiful. There's a gorgeous Keith Haring mural right near my house. The PMA, Barnes, Rodin and PAFA are all national treasures of are museums. The Philadelphia Orchestra, is and always will be, the pinnacle of great orchestras.
I love this city. I hate this city. I love this city. It's a bipolar town. When it's good, it's great, when it's bad, it's the seventh circle of Hell.
This city is just my size and energy. I could never live in New York when I have such a good life here. New York is too big, too many people, just as the french say "de trop." But I love visiting New York easily and cheaply for a weekend getaway at a friend's apartment in Queens.
Also, I hate cheesesteaks. Only tourists order cheesesteaks. The Philly "locals" go to is a pork sandwich with sharp provolone and broccoli raab.
Our gay scene is waning. Since I've moved here we've lost the bars Sisters, Bump, Pure (it's now a straight mostly douchy after hourse club), Key West, The Inn Philadelphia and more. The "gayborhood" is hardly gay anymore. Thanks, straight tourists.
We're a unique city, that's for sure, and I agree with OP - it's hard to figure out. We do have a creepy vibe too, but I think that's because of our revolutionary history. Surely anywhere you walk in Old City, you're walking on 250 year old graves. And they're still finding new ones.