Hey, thanks for taking a look. 
One thing I forgot to mention that I did do prior to this was remove all tracks from the library to redo the metadata tags in MusicBrainz (had crazy amounts of mismatches), then did Plex Dance on the library and re-added all tracks back into Plex.
Long story short, any cache on the server should be ‘new’ and is indeed working properly on the server (with new meta and album art) when accessed via browser.
Any reason you can see why Plexamp would be the odd man out in this scenario?
