True -- but that's a different issue. The original context of your suggestion made it seem like it was targeted to solving the specific problem at hand with less effort, so that's how I answered. But actually you were taking step back and looking at the broader context.
It's a relatively minor issue with us, because this server is lightly used in the morning, not used at all in the afternoon, and it's a VM -- so I take a snapshot at the beginning of the process, and I can always revert to the base configuration quickly if needed. Plus we do have a virtual template machine that we can generate new VMs from, and theoretically major updates should go on it first. However theory and practice can be different, and at this point the template is a few versions behind so it would take more effort to catch it up ... so nobody has done it. It's one of a number of maintenance tasks that management has not seen fit to allow time for.