SportScanner VS itunes_playlist_exporter

Use SportScanner. Get the naming convention from SportsDB.

I know it is here https://github.com/mmmmmtasty/SportScanner

I use SportScanner. Name your files the way they are named in thesportsdb.com

Create your own metadata agent that calls to your web server to get the image to add to the metadata. I'm not aware of any formal documentation that still exists for creating metadata agents. This archive of dev.plexapp.com might help: https://web.archive.org/web/20150113085312/http://dev.plexapp.com:80/docs/agents/models.html, but you may be stuck with looking at existing agents (like SportScanner.bundle) to see real examples of how to grab images for Plex to use.

Sports: https://github.com/mmmmmtasty/SportScanner (no longer maintained... I started an espn agent, but haven't finished it: https://github.com/ReenigneArcher/ESPN.bundle)

Trying to get SportScanner working without much luck. I had it in the wrong folders originally but got that worked out.

I assume you've got the Scanners and SportScanner.bundle folders in the wrong locations. The installation instructions are fairly clear.

Try SportScanner.

Executes a script which connects to iTunes, exports all playlists and uploads them to Plex.

Have a try of https://github.com/mrsilver76/itunes_playlist_exporter/

When I want to update Plex, I run a script that mirrors the local contents to my NAS. I also uses script (here) that exports all playlists out of iTunes and adds them to Plex.