Random problem in playlists

UPDATE June 2019

After Mac updated this solution didnt work any more. In general I started to hate mac, and have gone over to Linux. 
I can open an older / write a new M3U playlist with the normal texteditor, and save it as DOS-text. Some of the texteditors for Linux have this option.

OVERVIEW FOR NEW READERS SO YOU DONT HAVE TO READ THE WHOLE THREAD:

  1. Filename must be correct - example:   Music\Asian music\Kiha and the faces\Coffee

After I updated the Clip with firmware it is not any more necessary to write D:\

  1. You cant have a lot of filenames that start with the same - don’t write for example artist name in the beginning of the filename, then the playlist will just repeat one song.

So the playlist should look something like this:

The lines that go #EXTINF:274, young Iranian female voices

is supposedly not necessary. The number shows the length of the song, the rest are just tags

#EXTM3U
#EXTINF:274,Young Iranian female voices - nena
Musikk\Asia\Iran\Nena.mp3
#EXTINF:396,Young Iranian female voices - Masnavi Shoor
Musik\Asia\Iran\Masnavi shoor.mp3
#EXTINF:255,Young Iranian female voices - Heyf
Musikk\Asia\Iran\Heyf.mp3
#EXTINF:113,Young Iranian female voices - Longing
Musikk\Asia\Iran\Longing.mp3
#EXTINF:154,Young Iranian female voices - Farewell
Musikk\Asia\Iran\Farewell.mp3

So if you still have Mac you can probaly make it work if you find a dos editor