Actually, we have always booked our room first, then get the air. I guess it depends on how early you make your room reservations. Even before joining DVC, we made our reservations a year in advance because we knew where we wanted to stay. I would book extra nights, covering any possiblities for air. Then, after getting the air booked, I could cancel a night on either end if needed. Now that we are members of DVC we book what we plan to stay. A few times, I have gotten a flight coming into Orlando the night before our reservation started. Then, I just get a room at a hotel near the airport. It has worked great for us.