I can’t answer your first question, but I can recommend the utility MP3tag for editing the tags. It does bulk operations so you shouldn’t have to do your songs one at a time. And with the utility you may be able to figure out the answer to your first question by looking at the tags values displayed in MP3tag (find a song that says “unknown” on the Clip Zip, look at its tags in MP3tag, find the pattern, etc.).
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