- Yes, static playlists are supported.
- Yes, smart playlists are supported (caveat: to the extent that the rules can be mapped to rules in a Plex library filter). It’s important to note that nested playlists are not supported (e.g. playlists where one of the rules references another playlist).
- For smart playlists, it imports the rules, not a snapshot.
- There’s no automatic updating/syncing of playlists from iTunes. Importing from iTunes really isn’t meant to be an ongoing thing; it’s more for “moving from using iTunes to using Plex” rather than for keeping things in sync. (Right now, it’s currently only possible to import when creating a library via the GUI. A web app update due out soon will restore the
Import from iTunesaction on the Playlists page so that things can be updated for an existing library.) - Again, that’s not really the intent behind the feature. You’d have to manually kick off new imports to update things (once that action is restored in the UI).
(Note that being able to import static playlists requires that both iTunes and the Plex music library be pointing to the exact same music content with the exact same filepaths. If the path to a track in iTunes is different than it is in the Plex library, then the track would be skipped for playlist importing.)
