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help
since this is such an old post I'm not sure if you still require some help, but I can provide the answer of it least 1 of your issues. also I must apologize for mistakes in this reply because I am writing it with my phone and that doesn't work very well
I can provide the answer 4 the empty playlist issue first off I have to say that I don't use winamp but windows media player however I did have the same problem as you
what I did to solve it was to what location the files came from. I was absolutely sure that the files came from my mp3 player. but it seemed the player was loading files from the local drive. I then deleted files from that old playlist and then made sure that the new files came from my mp3. I checked the locations again and this time I was write and it worked.
hope this helps
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