Looks cool and seems like a neat idea. Seems like all the system are well implemented and there is a lot to do. Might want to consider adding all functions of IRL Windows to your's so people can manage it all better, like they do IRL.
Now, for my main issue: The pixel font seems busted. Check its ideal size and only scale it by multiples of that! Consider also not using a pixel font. They're terrible for stuff like Bold and Italics, which you may want to use a lot in this kind of game.