I started an MO homotopy theory chat room at http://chat.stackexchange.com/rooms/9418/homotopy-theory at the request of Jon Beardsley. there seem to be people in it already who know what the word "homotopy" means, so that is a good start. For now, i am the room owner, but we can fix that over time, once Jon gets his identities properly merged..
EDITTT: Jon's original room is now MO, which is more than I accomplished, go to http://chat.stackexchange.com/rooms/9417/homotopy-theory
Thursday morning: If you leave Meta and return, Jon's room is now visible on the middle right.