I’m in the process of re-building my Plex ecosystem. In the interim, I’ve either been listening to straight albums or playing from my iTunes library using this structure:

What this means…

“Un” is a folder of four auto-updating smart playlists. I shuffle the whole thing to listen (and of course, scrobble to last.fm).

• “Un 2023” contains all tracks released this year that have neither been listened to nor skipped
• “Unloved” contains all non-holiday 5-star/loved/favorited songs that haven’t been played in the last year
• “Unskipped” is a little more inclusive version of unloved, but limited to 1 GB of music (chosen by recently added): all non-holiday unskipped, undisliked songs not played in the last year
• “Untouched” is a little more inclusive version of un 2023, but limited to 1 GB of music (chosen by recently added): all non-holiday songs that haven’t been listened to, skipped, or rated

What it creates…

Overall, this is a mixture weighted toward top songs along with some “discovery” of recent music and recent adds to my library. It works very well with limited “management” of the music.