Slight Glitch
As a windows interface, you have the tendency to double click on icons on the desktop, When you do this, WMP will open Wordpad and Internet Explorer will open an error about WoW.
Aside from that, you had a good idea about MS Paint. The taskbar could be better in quality. There are also some action scripts that will make a text field display relating what time the user's real computer is set to (Just thinking of some ways you can make it more "believable" I suppose).
And as the person said before me, there is no depth to the game. Most of the programs don't even open. =[