Where are you getting $1000 from? He says 3 figure so it's in the hundreds, I'm assuming lower. Everyone has there point where they'd be fine burning the bridge. To me the ability to get a place quickly with an app from anywhere has a good amount of value, but I'd have trouble putting an exact price on it.

Read the article. He paid $1,221 plus for the new last-minute hotel. Got refunded $399.

Expected value takes into account probability. You aren't going to lose $1000 every time you use air bnb. Probably.