@mike_jones Yes! I tried out Strawberry but had to abandon it because I couldn't get the sort of smart playlists that I'm used to. Similar to you, I have a smart playlist that says:

• 3 star tracks that haven't been played in the last 2 years - Randomize and give me 30

• 4 star tracks that haven't been played in the last 2 months - Randomize and give me 30

• 5 star tracks that haven't been played in the last 2 weeks - Randomize and give me 30

• Unrated tracks that haven't been played in the last month - Randomize and give me 30

• None of the tracks have "[Turn off]" in the description.

Winamp accomplished this (without limiting the # of tracks per pull) by allowing you to edit the search string as a literal text string, and accepting parenthesis. So my WinAmp smart shuffle would look like (([Rating] = 5 and [Last_Played] > 14) or ([Rating] = 4 and [Last_Played] > 60) or ([Rating] = 3 and [Last_Played] > 730) or ([Rating] IS NULL and [Last_Played] > 30)) and [Comment] NOT LIKE '%[Turn Off]%'

MediaMonkey accomplishes this by allowing you to to create smart playlists similar to what Strawberry currently offers, but then you can also create a smart playlist that says "include these other playlists." So each one of those bullet points would be a smart playlist on its own (we'll just say they're named 3Star, 4Star, 5Star, and Unrated), and then you would have a smart playlist that says "Tracks that appear in playlists: [3Star, 4Star, 5Star, Unrated]" I generally tuck the "support playlists" in a folder out of sight, but really enjoy the flexibility of the MM model.

I am currently limping along with MediaMonkey in WINE because none of the native Linux players appear to provide this sort of playlist functionality.