Hmmm, you would need a working python installation which is as simple as grabbing an installer from
http://www.python.org/ , Calibre installed but that is a given I think, a commandline zip or rar program (to create the archive), and then try and run the dosage software.
Once you get that running the script should be easy to port to windows, these commands could be run from a batch script as easy as from a shell. It is the dosage program which is the crux - perhaps there is a way to grab offline copies of webcomics for windows already, in fact, I would bet on it.