Some songs in my playlist won’t let me play them. This song is not available in your country or region. This just recently happened.

Hello lmbmoore,

Are the affected songs obtained from the Apple Music catalog? If so, you may try removing the affected songs from your library, and then add them back to the library from the catalog once more. Then, try playing them again to see if they work well now.

If the songs are being matched from external media, such as a CD, try removing all instances of the song(s) from your devices, and then re-import/re-sync them from the original source.

If you continue to have issues, and have verified the song(s) are available in the Apple Music catalog, then you may try using this link to start a support request to reach out to Apple Support for further investigation: Get Support

Cheers.

I've got a similar issue. I didn't have payment info filled out in my settings when I sync'd my entire library (approx 80k songs). Songs I ripped from CD's give the "This song not currently available in your country or region" when I attempt to play them in a play list. They play fine from Artist or Song.