It's very SV-bubble to assume that Microsoft's security needs are more important than him getting his work done.
As he stated, he missed a critical deadline. What if the client cancelled the contract because of that, causing him to go out of business? How does trying to sympathize with Microsoft feed his family?
No, the tech bubble is not more important than things that happen in the real world. Windows has security problems? Sure, all operating systems do. But Microsoft shouldn't shift its problems onto the users. That's just bad business, and bad ethics.