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I live in Philly now and am furiously job hunting and applying to grad schools. Unfortunately I've reached the end of the ladder as far as my career in Philly goes. It's either move or wait for someone to retire. I've been here for 12+ years now. I'm not from here originally. I like it 90% of the time but I'm ready for a vacation (i've never lived anywhere for this long before).
The best way I can describe Philly to someone from the bay area is if you took SF, wrapped the east bay towns around it, wrapped the peninsula around that, and then you added 18 million people to San Jose (NYC). Basically, it's nice in the center, really crappy around it, really nice suburbs around that. If you're going north, there's no break in suburbs between here and NYC and it's a slow, 20 mile fade between what's clearly Philly 'burbs and what's clearly NY 'burbs and the people in the middle argue constantly. NY is winning. While most people here will tell you they don't like NY and most people in NY will turn their noses up in disgust at the mere mention of Philly we sure go back and forth an awful lot. There's something like 60 trains that go back and forth every day. Plus Megabus, BoltBus, Greyhound and, up until a few months ago, 3 different Chinatown bus lines all running multiple daily departures (the FTA shut down the Chinatown buses for safety issues).
So, I'll try to address most of the things that were hit on above -
Cost of living - dirt cheap. Compared to the Bay Area, compared to LA, compared to Boston, NYC or DC. It's cheap here. I live in South Philly, a block from the subway in a decent neighborhood a 5 minute walk to shops, bars, restaurants, etc. If I felt like walking to Center City it's maybe 25 minutes. City Hall is 35 minutes on foot. My house (a townhouse or rowhome - the terms are interchangeable) ca. 1880 is ~2000 sq. ft., 4 bedrooms, 2 baths and would probably sell for about $250k if we listed it right now (dated kitchen and no central air). We bought it 6 years ago for $200k. A slightly larger house (or brand new one) with all the mod cons would probably fetch $350k. Point is, you can probably afford to live in a much nicer neighborhood, much closer to the center of town than I do. If you work in the city and decide to live here you don't need a car although with two kids it's nice to have one. You certainly don't need two cars and it would be foolish to try. Getting rid of a car puts more than a little cash in your pocket every month.
Transit - People in every city complain about their transit system. Philly is no different. In my experience SEPTA is more comprehensive than BART/Muni/Caltrain and there's only one farecard. There are a ton of buses, 6 trolley routes, 3 subway lines, 4 suburban light rail lines and 12 suburban commuter lines (like Caltrain). One of the subway lines and one commuter line go across the river to NJ and one light rail line operates entirely on the other side of the river. Those trains are run by NJTransit and the subway line by the Port Authority. NJTransit also runs 10 or so bus routes into Center City. Everything that runs exclusively in PA is SEPTA. It's not expensive compared to the Bay Area or LA. Cash fare for SEPTA subways/buses/trolleys is $2. If you buy a bunch of tokens (yes, we're still using them for another year or two) they're $1.55 each. An unlimited ride monthly pass good on all transit within city limits is $83. If you're commuting from the furthest suburban zone (about an hour train ride out) the cash fare would be something like $8 and the monthly pass would be ~$155. Unlike LA there are few job centers here that are not near a rail line. If you're working in the city (unless your work involves docks or warehouses) your employer is not likely to be any more than 4 blocks from a subway or regional rail station. Even in the 'burbs most big office parks have shuttles to the closest train station (if they're not already next to the station).
Traffic - the traffic can be bad here but it's still nothing compared to LA, SF, NYC or DC. It's really only bad here on the expressways coming in and out of the city at the predictable times or when there's a major accident - or maybe headed down to the beach on the weekend. If you don't want to deal with it you can always take the train or live somewhere you only have to drive when you want to. I've made good use of the trains in LA but there are still large swaths of the city, particularly the west side, that you can't get to on a train and the buses take as long or longer than driving. It's hard to schedule anything there. I planned on meeting friends at a bar in Echo Park. One was en route from OC and 3 others had just left from West Hollywood. I left from K-Town, took the subway and a bus and was the first one there by 20 minutes. Our OC friend, with a 30 minute head start, got there an hour later. It once took me an hour to drive from downtown to Santa Monica then 90 minutes later it took me 20 minutes to drive back. Anyway, traffic is generally much easier to deal with in South Jersey. There are a lot more arterials and a lot less people. 50% of South Jersey is state and national forest and a lot of the rest is farmland or wetlands.
Schools - the schools in the city generally rank poorly (not much different from LA from what I hear) but, if you were to live in the city, I doubt you'd be living in a neighborhood with one of those bad schools and, the magnet schools like Girls, Central, and Masterman are among the top 10 high schools in all of Pennsylvania. There are grade schools with similar creds. so don't worry. You don't have to pay insane money to send your kid to a Quaker school. Getting your kids (yes, I have them) into a good school requires a lot of research, due diligence and patience but it can be done. Suburban schools are generally better than the city schools but there are still bad schools in the suburbs too. The best high schools in PA can be found in Bucks and Montgomery and parts of Chester County. In NJ they're in central Camden County and adjacent areas of Burlington County. It's definitely not like LA here. Philadelphia the metro is about 6.5 million people. The city proper is 1.5 million and only covers about 140 square miles. Assuming not much traffic you can leave Philadelphia City Hall and be out of the city in 10 minutes and in one of the best school districts in NJ in 20 minutes. Add 5-10 minutes for one of the best in PA. At rush hour it might take you 45-60 minutes in a car but always 20 minutes on the train. I guess in that regard it's not much different than SF.
Weather - I'm familiar enough with LA and SF to say the weather here is nothing short of extreme by comparison. We're at the same latitude as Fort Bragg, CA and Reno, NV. Take Fort Bragg's rainfall and mix it with Reno's temperatures and that's pretty much Philly. Mid-June to mid-August is really hot and humid. Unless you're gonna be commuting from Atlantic City, central air is a must have, must use. This summer was the 2nd hottest on record but we do usually get some cooler days mixed in. This year, not so much. 85-90 is the normal high but high 70s to mid 90s is not out of the ordinary. January and February are typically cold and wet. Average high in the low-40s. The big deal is that we can have a few days in a row where the temps don't break 30 then a few days later we can get weather in the high 50s. Snow is sporadic and rarely sticks around that long. Last winter snow fell for a few minutes just after Halloween (didn't stick) then it didn't snow again all winter. Last winter was also the warmest on record. The winter before that we got close to 5 ft. of snow in less than 10 days. How much snow we get depends a lot more on how much Gulf moisture we're getting and a lot less on how cold it is. Also, the city has a distinct micro-climate owing to the urban heat island. It rains here a little less and it's 5-10 degrees warmer than surrounding suburbs. That goes for the winter the same as summer. It's not uncommon this time of year for it to be 15 degrees warmer in Center City than in Atlantic City.
Beach weather here generally runs from early May to late September. The water is usually warm enough to swim in (mid 60s to upper 70s) from mid-June to mid-October. October is a great time to go to the beach. More often jeans and hoodie weather but OK for a quick dip. I've been to LA quite a bit. On different trips I've been there in May, June, November, December and January and the water has never been warm.
Culture - some families here go back hundreds of years. Most families are at least 4 generations. My wife's family came from Holland in 1770 and settled 3 miles from where we live now. Most of the family stayed in that neighborhood until 1950! Except for a few retirees who've moved to Florida or the Carolinas they're all still within 20 miles of there. Point being, most people here have huge extended families that live nearby and dense, layered social networks (not the virtual kind) that are generations deep. People aren't in any hurry to be BFFs with someone they just met. That doesn't mean that people aren't friendly - just don't expect to get invited to a kid's birthday party right off the bat. They're probably trying to figure out what relatives to not invite to make room for the friends they've had since high school. The flip-side to that is, once you're in you're in. Expect to get invited to everything and expect for people to be offended and cut you off if you decline more than a few times. If you're living in the city you're much more likely to be around other transplants and transients - especially in and around Center City and in Mt. Airy. If you are in the city don't be surprised to bump into people you know all of the time. If you're here for a few years don't be surprised to get your own 6 degrees of Kevin Bacon whittled down to 2 degrees. (I actually had lunch with his dad, Ed Bacon, in 2004 so there you go.) Seriously though, since so many people have such deep roots a lot of social circles start to overlap and you'll start to hear people say "oh, how do you know so-and-so? this town is too small/incestuous/smallest big city ever" etc, etc. I don't know if it's like that in SF but I know it's not the case in LA. It's not that it's actually small here. It's that the area where most social/cultural activity takes place is very compact and if you get out and socialize with any regularity you can't avoid that phenomenon.
We do have towns and neighborhoods where people are all about keeping up with the Joneses but here you'll find much, much less of that bling-bling, ostentatiousness that people talk about so much in LA. It's what Philadelphians dislike about NYC so much. Culturally, this is still very much the Quaker City. Modest, self-deprecating, self-critical and consensus driven.
Food - this is an awesome town for food with a lot of great restaurants. The last decade and the last 5 years in particular have seen a huge boom in the quality and quantity of restaurants here. Bourdain just shot the Layover here a few weeks ago. Not a huge fan of his but I'm psyched to see the show b/c allegedly there are no cheesesteaks in it and no shots of anyone running up the Art Museum steps. It should be a good intro to the food scene here for any outsider. I'm not gonna gonna name drop this place or that - that's what google is for. Is the food scene in LA more dynamic? Probably. I hope so. It's a much bigger city. The stereotypical Angeleno thing to say in Philly is, "you can't get good <insert mexican dish> here". Seriously? Have you seen a map? I could only imagine the shoe being on the other foot. Some mexicans from Puebla (where basically all Mexicans in Philly come from) hanging out in Baja saying "man, you can't get good roast pork here" My other favorite is "these <insert tropical fruit> are terrible" Seriously? I don't know what to tell you, they say "product of California". Can you get good mexican here? Definitely. Will every taco truck blow your mind? Nope. Also, pizza here isn't that great and a lot of Philadelphians know it because they get pizza in NYC and North Jersey enough to know the difference. Don't get me wrong, you can get good pizza here without trying too hard and even the mediocre places here are better than the best down south or in the midwest but they're still mediocre. You have to go up to Trenton to find people taking it more seriously. The pizza belt runs from Trenton, through NYC and on up to New Haven.
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