Take a look at something like http://www.cutepdf.com/Products/CutePDF/writer.asp

Consider the AT command for scheduling jobs on windows.

AT will not work if you don't have a command line. Consider looking at video game hacks. I remember a Ultima Online hack that used Macro.exe from windows 3.1 to interact with windows online.

Let me know your progress I have lots of suggestions. But wife just called so gotta runnnn