Congratulations on solving your question about repeating audio file entries within a Playlist text file.
Your detailed explanation inspired me to explore the possible differences between end-of-line characters used by TextEdit (Mac app) and Notepad (Win exe ). I think the Mac end-of-line character produced by TextEdit (LF only) is not compatible with the end-of-line characters that the Clip Sport (and Clip Jam) require to properly read successive lines in Playlist files (CR and LF).
Your clever solution is to clone a text line produced by mp3tag and then change the internal information without deleting the hidden end-of-line characters (for CR and LF).
Here is an introduction to this complicated topic.
https://www.editpadpro.com/tricklinebreak.html
There are likely a wide variety of solutions to the Mac TextEdit end-of-line limitation for your needs. Here are two.
1) Create a simple text file with several end-of-line entries copied from a working Playlist file. Use this separate file as a “copy and Paste” resource for your future endeavors.
2) Use the text editor app NOTEPAD++ that is available with “Wine Bottler for OSX”
http://winebottler.kronenberg.org/
(Wine Bottler is the app the authors of mp3tag use to make their Mac-compatible version.)
