Why I think the people on Airbnb are 'cool' is that its a small population that has a lot in common (young or young-at-heart, singles and couples without kids, internet natives, own a macbook, would love to hitchhike Europe while submitting correspond reports for the NYTimes). As it grows, I'm worried that everyone's not going to find everyone else 'cool' on Airbnb.
I wasn't around for the early days of Craigslist, but I imagine it was easy to like people you found on Craigslist because they were probably very similar people to be on Craigslist so early. But now, after scale and popularity, that's gone.
I wonder if Airbnb might lose the 'cool' people edge after scaling.