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Notes -
I think this is a fundamentally hard question: "How do we design the system to give incentives to maximize the robustness of infrastructure in the public commons?". I don't have a complete answer here, but it's easy enough to point to failures on both sides of this sort of thing: there has been no shortage of major incidents stemming from unpatched systems on the Internet. This seems like the first major incident in which the systems we put in place discourage that (automating the rollout of security fixes) have, themselves, failed.
I don't think a perfect solution exists today. The NIST guidance to keep your systems updated and install AV is better than nothing, but no checkbox-based system is really substitute for a good head on one's shoulders aware of what's going on. I think there is good discussion to be had about what the rules and incentives should be, but unless your system is "hire smart, capable, competent people", and really even then, I don't expect perfection. And honestly, our really smart, capable people are probably better utilized working on harder problems than IT security for non-life-critical systems.
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