Do you know if the script runs without error? What I do sometimes is put the script into controller.py and try to run it from there. My only guess at this point is perhaps there might be a permission problem writing to the "cron" directory.
In your Windows Task Manager can you see that multiple python processes are running? To make absolutely certain, you might want to kill all of the python processes (or restart Windows) and then watch your Task Manager as web2py starts up.
