A while ago I booked a room at a halfway decent hotel. It wouldn't be the first time I've stayed at a nice hotel, but it was the first time I booked a room for myself instead of paying a friend $50 to sleep on the tile floor of their nice hotel room. A week after booking the hotel, I booked flights for my girlfriend and I. Since our trip would be to the Caribbean at the height of hurricane season (the nice hotel was cheaper this way), I did something else I've never done---bought flight insurance. This week my hotel canceled on me, also a first. But, what's this...I booked the flight insurance, so, definitely for the first time in my life, I would not lose out to the airline. Then I found out that my flight insurance only gives back about half your money in the event of cancellation. So in the end I netted out spending several hundred dollars only so that I could spend several hours on the phone and on email trying to get money back. This is why I stay at the cheap hotels.