Because the price changes of flights are not the kind of catastrophic loss for which insurance programs make sense it becomes more of a gambling paradigm than an insurance situation. Level Skies's algorithm tries to make them money. In terms of pure dollars you have to make a rational purchase here your expectation needs to be that your planned purchase parameters will be outside their model.
The ONLY way this can be a win for a consumer is if the utility they gain from the satisfaction of having some certainty around price is worth the fee level skies charges because on average you shouldn't expect to make money on the purchase.
A change in price of a few tens-hundreds of dollars in an airline ticket is not subject to the same kind of loss function that makes home owners insurance a smart idea. IMHO.