Random problem in playlists

Hopefully this little exercise is beneficial for both of us. You just taught me the drive letter is not relevant.

Edit your text file “Kill me heal me chicago.m3u” and delete the entire first line.

Then re-save as a text file (ends with .m3u).

This m3u file can be saved in the Music folder OR the “Kill me heal me chicago” subfolder.

If this works OK for you, we could discuss the batch file process and how to execute using the Wine.app on a Mac. 

If you have mp3tag working on your Mac, then you likely already have Wine installed.

Alternately, you could use the Textedit.app and revise your future m3u files (from mp3tag) using the simple style shown here.

Please write back with your results.