I've talked to her about funding and she's told me that just about every Ph.D. student get very livable funding for 5 years (and tells me the average student takes eight years to finish; after five years most have to teach or look for some other outside source of funding) and it doesn't seem that the recession has much affected their ability to fund. I don't know specifics about health insurance and the like. I haven't talked to her much about housing either but I have walked around West Philly pretty extensively and it seems that a lot of grad students live in very nice, cute houses in the general vicinity. I haven't talked to her at all about applied/activist bents to anthro research (not really my thing) but if you look at the website it seems like several undergrad courses integrate activism into their work so if it isn't an overarching focus of the program then at least there are likely some interested/knowledgable faculty. I've had the opportunity to meet a lot of the current grad students and they all seems very friendly and supportive of one another, very familiar with one another's projects. I thought that was great. Reviews of faculty friendliness, approachability, helpfulness, and the like were mixed: according to the students I spoke to, there are some awesome faculty members and some who weren't so awesome (unsurprisingly). UPenn is a pretty integral part of Philadelphia. University City connects to center city Philly via a five-minute SEPTA ride and the relationship between UPenn students and faculty and West Philly residents unaffiliated with the university seems to be improving every year (you can google for some of the initiatives they've taken since the 1980's, there's a lot of info). Campus security is also pretty fantastic. If you walk around University City at night, you'll likely feel very safe (this is something I've done on many occasions; I'm an undergrad in a Philly suburb and so have spent a lot of time in the city).
As for departmental focuses, apparently although UPenn is known for its strength in Central and South American Anth and Archaeology, a lot of the faculty who brought this renown have retired recently, although a few still remain. I just earlier this year realized that I want to do Anthropology and I'm still trying to figure out how all of the sub-fields break down, so I apologize for not being incredibly knowledgeable or helpful in this topic. From what I gather, they're very strong in physical anthropology as well as cultural anthropology and historical archaeology. This is obviously a "duh" thing to say, but you should definitely check out the faculty profiles and graduate courses offerings if you haven't yet.
Also check out the UPenn Museum of Anthropology and Archaeology, which a lot of grad students (and not just anthro students) become involved with, either merely as a resource for research or in a more hands-on way, developing exhibits and becoming involved with the behind-the-scenes works, etc.
Sorry so much of this is vague. I'll ask her your questions and get back to you with more specific and helpful responses.