The main trouble is that for it to fully work, you need to have the big corps bidding against black hats in this market. I can't see that happening. It'd have big corps dirtying their hands too openly.
The other trouble is that a lot of the damages (or value) of software bugs aren't readily fungible to dollars. For example, to actually profit from the Ashley Madison hack you'd need to blackmail a whole lot of people, which is incredibly time consuming. So software firms would be able to underpay for most exploits: The amount they'd be have to pay is at most what a black hat can profit from the bug, which is necessarily less than the real damages because the black hat has to cost for fungibility.