Firstly, thanks for taking the time to look at this for me 
Just on a quick note, these two topics are where I read that that the library path needs to be the file path and not just the folder path:
https://forums.plex.tv/t/why-can-i-re-import-playlists-in-macos-but-not-windows/623665/5
https://forums.plex.tv/t/how-do-you-import-playlists-from-itunes-to-plex-server/489577/24
I deleted the library and then imported it again, the logs are attached.
