I'll be attending Pitt this fall as well. My wife and I are probably going to buy a house or condo, we'll be up at the end of this month to start looking. Half of her family lives in Squirrel Hill and it's nice, but others are right - there's more life in Shadyside. The Southside can be difficult to commute from but seems to be lively and up and coming... of course the strip district has great life but not sure if it's where you want to be during school... we've looked a little at Lawrenceville but the commute would be difficult by bus and it's a little too rundown for us. Regent Square is an area we're looking in, as well as Greenfield, which is not the happening-est place in Pittsburgh but fits us nicely.