I respectfully disagree - I do agree that the natural financial death of a company probably shouldn't result in bailouts, but if I as a company get breached because my fully-updated, follows-best-practices Windows Domain got hacked because of a vulnerability in Microsoft's stuff? That's hardly fair.

Shouldn't I be able to sue Microsoft for financial relief?

That is an acceptable outcome. Life isn't fair. Companies fail all the time for a variety of unfair reasons. This will force customers to demand that Microsoft and other software vendors improve their own security practices and/or indemnify customers for damages from breaches. You can sue Microsoft for financial relief if they breach your contract.