Come out of the Auto Update cave and into the light
That's by no means an exhaustive list. Some problems are inevitable when you're dealing with a Windows hardware and software gene pool that looks like the La Brea Tar Pit, but I think you can draw three important conclusions:
First, patching Windows is hard.
Second, Microsoft needs to do a better job of tracking and reporting on problems as they appear.
Third, for Pete's sake, set Automatic Update to Notify but Don't Download on any machine controlled by a reasonably savvy Windows jockey.
If somebody tells you differently, point them to this list. If they're still convinced Auto Update is the way to go, ask them to refrain from dragging their knuckles on the floor.