Shared Playlist or Compilation Album 'Item Not Available, This item can't be played' problem happens a lot when listening to a shared playlist.
As to iOS, it's recommended to upgrade iOS to supported latest version for your device. On Mac, you can simply upgrade iTunes via Mac App Store.And, even after 'clearing unpinned documents' the list is still there, and an attempt to left click gives 'The item you selected is unavailable. There is no right click 'Remove from list' command anymore. Even more confusing is that after clearing 'unpinned documents', the document names are still there. Just FYI, this is happening to me also.