Couple of qu's to try and pin down the behaviour you are seeing:

Are you storing your music on a NAS rather than on the same box that
Slimserver is installed on ?  I guess so from your reference to
D:/Music.  If so, what is the value that you have input into the Music
Library setting? Is it something like D:/Music...?

Have you done a full clear and rescan before trying to play the
playlist?  If you do a full clear and rescan, do the songs still play
twice or does only one of them work?  

You mention the Guess tags feature: are you using this for part of your
library (i.e. is some of it untagged) or are all of your files tagged?
Slimserver should only guess tags using the folder structure if there
are no tags available AFAIK.  Not sure what it does if some files are
tagged and some not.

Could there be any symbolic links to other parts of your music library
or a shortcut ?

I also came across this thread which perhaps describes something
similar to what you are expericing - although it could be specific to
WMP playlists.  If you replace D:/Music...with //[mediaserver]/Music
(i.e. the full network name) and do a full clear and rescan, then line
up a playlist - do you still get two copies of each song?

http://forums.slimdevices.com/showthread.php?t=19638&highlight=duplicate+entries+playlist


-- 
Siduhe
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