Hey there,
Thanks for testing. I found a free, time-limited windows VM to test with, courtesy of Microsoft (https://www.modern.ie/en-us/virtualization-tools for others who may be interested). Which allowed me to at least attempt to start up the script and provide some install instructions for windows users.
1. Download and install Python 2.7.x from https://www.python.org/download/
a) Ensure you enable the option to install Python to the system/site path.
2. Download the zip of plex-lastfm-scrobbler from https://github.com/jesseward/plex-lastfm-scrobbler/archive/master.zip . Note a made a couple changes to support windows, so you will need to grab a new version.
a) unzip to a temporary location. for this example we will use c: emp\plex-lastfm-scrobbler\
3. Open a command prompt and change to the emp folder
cd c: emp\plex-lastfm-scrobbler\
4. in the c: emp\plex-lastfm-scrobbler\ directory, run the installer from the dos prompt
python setup.py install
The above command installs the python scripts to various locations. Directories of interest are
* c:\Python27\scripts\
* .config - this directory is created in your Users home directory. You will need to modify the configuration file from within this directory and point log locations at the appropriate locations for Plex on windows. You can set the "log_file" property to c: emp or some other location which you wish to write logs to.
To run the application, do the following from a DOS prompt
cd c:\Python27\scripts python plex-scrobble.py