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Wow. I had no idea Philly was such a beautiful city, those videos were very pleasing to see. I could just walk around for hours every day and never get tired of looking at buildings like those. It's not overkill, I enjoyed them.
Combined with the plentiful schools and the prospect of being able to take day trips to NYC when budget permits is truly tempting. I really did not expect such a solid consensus, but I'm excited that there is one. I'm open to more input but it looks like it's Philadelphia.
As others have said, Philly seems like a good choice for you, but I would also reccomend you consider Washington, DC. The biggest downside to DC is the cost of living...but it is cheaper than NYC, San Fran, Boston, etc. And it hits all your other desires.
DC has a good variety of colleges (both in the city and in the nearby areas), great public transportation and is very urban feeling (although, not "tall", it is very dense). It has a good vibe and there are lots of young students/professionals. I also think the climate is slightly better than Philly. You would be slightly further from NY, but still plenty close for a day trip. And it is a very pretty city...lots of trees (cherry blossom festival right now).
One more city to consider, and this one is thinking a bit outside the box : New Orleans. The city has several good colleges (Tulane, Loyola, Xavier, University of New Orleans, etc). The cost of living is quite reasonable. The population is not huge, but it really does feel like a real city...parts are very dense and there are areas where you can live without a car and either walk or take the streetcar/bus. It is in the South, but does not have a conservative/Bible Belt feel to it at all (the influence there is more lapsed Catholic than fundamental Baptist). Maybe not your exact cup of tea, but I figured you would get a ton of suggestions for East coast places and figured I would throw out something a little different.
Hmm the cost of living in DC is a bit higher than I'd like. It may be offset if there's better transfer programs at the colleges, I'll definitely look into it.
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