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I don't really see it as a real estate site, more of a review/opinion site like Yelp or Angie's List. I don't think you will have much luck advertising in real estate, this is something that kind of needs to catch on to really grow. Your target user is likely to be 18-25, so I would look at larger college markets to start. I would actually pick a state like Texas (California is too saturated with new tech crap to make a blip), identify a few sub-markets like Houston, Dallas, San Antonio and Austin, then advertise where college kids in those places are most likely to see it. Once you have built up a decent database of listings, you could publish locale-specific compilations and have universities hand them out to incoming students with their orientation packets - I actually did that with a different business to get it rolling and it worked quite well.
You will likely encounter the usual chicken and egg scenario that any user-generated content business hits and that is not enough content to bring the users and not enough users to bring the content. The good news is that once you build up a critical mass, the problem will solve itself. The bad news is that you have to figure out how to attract that critical mass.
One last thought - you will probably end up having to police your listings carefully lest you find yourself a defendant in slander or libel lawsuits.
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