Last question first:

Wendy flags can only be applied to songs, not to playlists. This is by design.

Automatically repeat question:

When you set the playlist to automatically repeat, did you do the following:

- Remember to synch up with your player after making the change.
- After the synch, go in and specifically select that playlist from the "playlists" menu.
- Allow the playlist to play all the way to the end.

Are all the song files in the playlist good? Is it stopping on a bad MP3?