So quick and random update for any future Google searches that mention this problem.....
The monitor issue turned out to be gpu related. Not really sure how it would've happened via updating from 7 to 8, but I just got a new GTX760 to replace my old AMD5770 and suddenly the monitor turns on with the PC and it enters automatic sleep mode properly (used to only shut off the monitor but comp would remain on), albeit a few seconds longer than it used to.
As for the programs not appearing, like another suggested a re-install of the game itself did help. I'm unsure if uninstalling Steam would fix them all at once or have any effect, but I had to clear up some space anyways and just uninstalled several games and left the few I had already re-installed.
So that's that, questions answered!