I am really sorry you are having so much trouble with playlists. Especially since you are making a serious effort.
I have a few simple suggestions for you to try.
1.Try using a very simple text editor app on your Mac. Save the file as .m3u. Save the file as a simple text file; not rich text.
- Try creating a simple m3u file based on 3 audio files saved in a new Subfolder under the main Music folder.
Save this new text file in the new Subfolder with the filename: Simple.m3u
Music\Subfolder\audio file1.mp3
Music\Subfolder\audio file2.mp3
Music\Subfolder\audio file1.mp3
Music\Subfolder\audio file3.mp3
Music\Subfolder\audio file2.mp3
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I hope you are able to create this simple m3u file and it works in your Clip Sport.
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The best way to create and enjoy playlists on a Clip Sport is with a software method. My current favorite method is to use a batch command.
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When you want to introduce special repeat and play patterns, this is a bigger challenge.