PSAE testing

Today was the first day of PSAE testing. It went well. A boring day, though. Proctoring is no fun. Now, the other CI teachers and I are planning a project for the last 6 weeks. We're going to do a career / college project, but the planning process is a bit overwhelming.

I looked at condos this past weekend. I really enjoyed it. There are a few different places I'm looking. First, I'd like to be in Bridgeport, get Sox tickets, and spend the summer at baseball games. The first condo was in Bridgeport at 35th and Halsted. It was about 800 sq. feet. I loved it; I could watch the fireworks from Sox park from the balcony.
The second that I liked was on Cullerton in the South Loop. It was cool; a little smaller than the first one, but it was within walking distance to Soldier Field and downtown. I didn't see many others I liked. I'd like something a little bigger, but I can't afford it. I'd love to get a two bedroom because I can guarantee that Emily, Jack, Tori, Abby and others will all want to spend the night at some time. I'm sure Em and Tori will want to come at the same time. I just don't know what to do.
Should I buy a house in Cal City and be close to work and have more room? Or should I buy a place in the city but sacrifice my commute and condo size?

Happy Earth Day!