So if I'm understanding this right, these changes are happening because of limitations in a new CMS, yes?
Then it sounds like you shouldn't move to this new CMS. In the tug of war between headaches for the hundreds of Windows Update team members versus headaches for the MILLIONS of IT pros out there, I think doing what's best for the customers takes precedence. So let's do everyone a favor: hit the pause button on the rollout.
Honestly, the reasons that you've given seem trivial to fix. I mean, come on, even the URL for this article has a numeric ID: 2146594. How hard can it be? All reasonable CMS will allow you to control the format of the URL, and allow you to template in specific data in each document. It's incomprehensible that Microsoft cannot have these features. You're MICROSOFT.
Unless, of course, there are ulterior motives for this otherwise inexplicable change. Is there something you want to tell the rest of the class, Christine?