The breakage that sticks out to me is that IIS in Windows Server outputs some reports as XML+XSLT and these have become nigh unusable for years now.

I ignore every official statement about “support” and simply look at the horse's mouth: Microsoft hasn’t bothered to fix this in IIS, and likely never will.

It’s a dead product, “supported” only in a contractual sense, not a practical one.

(If you called support right now demanding fix for this, they’d tell you that it’s broken by design, have you tried moving to a recurring revenue service offering?)