You could handle all the rebooking stuff over the telephone or online, so that's not a problem. If a flight is cancelled and you're offered a hotel it gets complicated. Then you have to go through the trouble of buying another refundable ticket and canceling.

The chances of this working are very high, but I don't understand how it would be worth the hassle. If you do it constantly you will get caught, if you do it once you don't save all that much.