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HUP is surrounded by Penn's campus, and Drexel is nearby. Large swaths of West Philly are gentrified, but large swaths are still tough neighborhoods.
Yes, the Main Line is generally very expensive (though Ardmore is more affordable; so, too, might be Wynnewood). The R5 regional rail line runs through the Main Line (it's the old "Main Line" of the Pennsylvania Railroad, hence the name) and provides easy access to the city. Also, the light trolley runs through parts of the Main Line, and ends at the Market Street el/subway, which takes you right under Market Street and would be pretty convenient to HUP. Other suburban areas to check out would be Media, Swarthmore, and Wallingford (7th best place to live per Money Magazine's 2007 ranking), though their taxes are generally very high and if you are from MO I assume you will think the housing is expensive as well. Also, Havertown and Broomall are also fairly convenient to the city, are more affordable and not generally snobbish. Also, depending on where you are from, you may find some of these communities a little on the congested side.
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