It's tough because people don't exactly look for new houses every single day so coming up in their brain as the app/site of choice when they do need a new house/apt is difficult. I would hate to do a "better apartment finder" startup in this space (airbnb excluded).
I think craigslist grew pretty slowly over the course of a decade, right? Not sure there's a recipe for overtaking them quickly that doesn't involve using their data/userbase in one form or another.