Welcome to Windows 8 Forums, "The Void" - After the Black Sabbath song, or episode of Star Trek Voyager?
If there is a Windows.Old folder in there, it may have not strictly been an "Upgrade" install, it was maybe a fresh install, and the old User and Program files files were moved to "Old". You get the Choice of what kind of install you are ding, you get "Upgrade" which will keep all of your folders and files and programs, or "Clean Install" - Windows 8 Should have offered you both, but if you had a Disk with Media Center already installed, it would NOT have allowed you to do an Upgrade, you would have been forced to do a Clean Install.
A successful Upgrade may create an OLD folder, but it should be empty. That's the way it was on this very machine, because I upgraded it from 7. EVERYthing that was on my desktop in 7 got moved to 8, and they all worked. And after the next Reboot, the "Old" folder vanished.
He may not have a restore point, unless he ,made one before he moved those desktop items back.