Hyperlocal seems like a can’t-miss proposition. “There is real demand for good information about our neighborhoods, our children’s schools, our streets, our blocks,” says Jay Rosen, an NYU journalism professor and media blogger. Except for one thing: Success remains perpetually around the corner, constantly predicted yet never fulfilled.

A good look at some of the challenges in the hyper-local space and how some companies are addressing it. I don’t think the winner will come out of a news organization. The winner will figure out how to replicate the gossip, conversations, and community organization that already exist in neighborhoods and make it easier for people to find and participate in those conversations. Maybe it will look something like this.