Apple’s Music.app has a feature where you can create a Smart Playlist and you can choose x many tracks to fill the playlist, and includes a random function.
Plex allows you to create an advanced filter and you have the “Limit to” option, but it only fill it up with the first x tracks, you can’t set that to random.
Why this is helpful:
My Sonos system doesn’t like playlists that are too long for alarms. So it just plays the default “Sonos Chime” in the morning instead of music.
I figured out the problem was playlists with over 1000 items (approximately).
That doesn’t exist in Music. (I’ve confirmed it does in Movies, I thought perhaps it was because it’s in list view and not poster view, but don’t seem to see a place to do that in Music)
It exists if you switch from Tracks mode to Artists or Albums. You can still apply the track filter options and by saving the output to a smart playlist, it’ll be a list of tracks anyway (even if the immediate result of the advanced filter will only show you the artists/albums with those matching tracks)
Edit: I was worried for a moment if the Limit to will properly translate to the number of tracks if you set the filter to display albums or artists – but apparently it does
As stated above… you had created the previous version of your smart playlist based on Tracks mode. Tracks mode only supports table view – so editing the playlist’s filter will bring you to what your video shows.
You could have set the mode to Albums or Artists while editing the playlist filters (which will also give you the Random sort option.