It also becomes a much more interesting market if there are multiple competing providers of insurance that bid against each other (just as ad networks work, for example).
As a buyer of insurance, I would always have the choice to not buy the contract and take on the risk myself.
If the market works (which is a big if), it should become an efficient transfer of risk to companies that are experts in evaluating it.
Very interested to hear more of your thoughts though, as you're obviously part of the target audience at your dayjob!
The tradeoffs are pretty obvious to merchants when they compare their authorization rates between processors and look at the revenue the lose, either through fraud or through false positives.