Quick update - that patch you provided was installed last night without issue. However, on the subsequent reboot it took what I'm told was a very long time to complete and successfully boot into the OS. (I'm not the guy patching this server so I'm being told this in response to the questions I'm asking.) He said after it came back up he checked to see if there were any updates to install and there were none but he rebooted a second time just to see if the long boot time was a one-off. He reported that the server again went through the motions reporting it was installing updates and took 30-45 minutes to fully boot.
So I don't know what's up with that or even where to begin on changing that behavior so any feedback you have is greatly appreciated.