the total amount of payouts per flight is limited as well as premiums and individual payouts. there is a non-negligible legal risk of such action and the payout limits in the end will converge to the price of the risk someone is going to take.
Ironically, your system is meant to help compensate people when delays to flights occur yet to me it looks like you've built something that strongly incentivises people to cause more disruption to flights.
I think we will find a way to deal with those issues. Experiments like these will help us (and society in general) to come to the right conclusions. Of course we should be careful not to cause too much harm on the way.
Also see https://www.reddit.com/r/ethereum/comments/529o5p/flightdela... and the discussion there.