This appears to be the problem:
Nov 20, 2020 20:45:30.097 [0x700001626000] Debug — Request: [127.0.0.1:56960 (Loopback)] PUT /playlists/import/itunes?sectionID=null&force=1 (11 live) GZIP Signed-in Token (Simebaby)
Nov 20, 2020 20:45:30.097 [0x700001626000] Debug — Could not convert null to the correct type
Nov 20, 2020 20:45:30.097 [0x70000141a000] Debug — Completed: [127.0.0.1:56960] 400 PUT /playlists/import/itunes?sectionID=null&force=1 (11 live) GZIP 0ms 463 bytes (pipelined: 6)
In case this helps anyone - this is how I got this working (the method was taken from another post on here so I take no credit, but I can’t find the original now):
Click on the three dots on the right of the music library (not playlists), then manage library -> edit.
Don’t make any changes, and save. A scan of the music library will run.
Import playlists as normal. Note that you’ll need to export your music library to an XML file manually if using the Music app - and Plex looks in the ‘old’ iTunes’ location - so /Users/username/Music/iTunes/iTunes Library.xml on a Mac, not sure on Windows.
That got it working for me. I’ve tested a few imports and all looks good. You’ll need to come out of playlists and go back in to see any changes. If it stops working I would hope the refresh of the Music Library would get it working again.
Hope that helps someone.
Si