This sounds like an insurance problem.
You've got events that occur rarely enough to an individual (company) that it's hard to work out what the best course of action is using the limited data that an individual can gather.
If there were, say, a half dozen major security companies that everyone subscribed to one of, and they each published their statistics showing how many of their customers suffered various kinds of security breaches, this market might look much less broken.
You could potentially get to that state by having some major existing insurance companies offer "digital threat insurance", and require anyone who claims on it to be using the security services provided by one of their vetted providers.
Yes, you'd be building the sort of major corporate bureaucracy that HN hates, but you'd also be properly aligning everyone's incentives, and shifting the responsibility for the Hard Problem of determining who was selling real security software to a smaller number of better-resourced people. Perhaps there's a reason why major corporates are the norm in big, serious markets.
Edit: disclaimer, I'm an armchair theorist and have no skin in the game - perhaps this already exists or there's a good reason why it doesn't work