Managing Music on Classic iPod
Is there a way I can sync my iPod Classic without losing all of the songs that are on it? Up until the latest update I could add to and edit my playlists on my iPod.
iPod Classic
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If you've upgraded to macOS 10.15 Catalina then the options for manipulating playlists directly on the device that used to be present in iTunes are no longer available. You can add playlists, albums, or tracks from the library to the device, and you can remove tracks from it, but that is about it.
See Recover media from an iPod - Apple Community. Pull everything into your library, manage it there, sync what you want to sync back to your device.
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