Kirk McElhearn posted a great article on MacWorld back in 2013 about complex playlists. Went to try to implement a playlist following his directions and failed: there is no All/Any option for smart playlists in iTunes 12.8. I remember doing this successfully once. When did Apple remove this logic?
You can still do Any/All. When you create a new Smart Playlist, there is a template for the first rule with a Plus button for adding more rules. If you hold the Option key while clicking the Plus button, the new rule is added with an Any/All selector. You can make complex rules by Option-Adding even more rules. You can delete the first rule if you want the Any/All choice to apply to all the rules. (This Option-add method also works with Finder Smart Folders.)
Fabulous. Thanks for the tip.
As an aside, if your smart playlists rely upon “recently played”, don’t use AirPlay 2 as there is a bug updating play counts.
See for instance:
For a while, using my HomePod caused havoc to my smart playlists, but once I stopped streaming to it, the “last played” and “play count” fields worked again.