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First of all , I would recommend you to format the drive once after you backup your song files.
Then try loading the files once again , if that does not work , try formatting the drive with a different format , for e.g. FAT32 , this option you will find when you connect your drive via the MASS storage mode through a cable and then right click and then select format option.
When you have formatted your drive with this other format, make sure you copy the files back and then try testing it.
If that does not work then what you can do , is try limiting the number of songs, in one particular folder , for e.g. Put 10 files in one folder and the other 10 in the other folder, this could give you an idea as to how the file system is made up, and then you can copy the files accordingly.
Hope that helps ...:) In case you have any queries, feel free to contact me.
MP3 player with LCD 1 GB flash memory and USB drive
high-contrast LCD display with 7-color backlight
plays MP3 and WMA digital music files, ID3 tag support for song information display, mobile data storage function
convenient integrated USB plug( no cables required)
USB 2.0 hi-speed for fast file transfers
Coby MP300-1GBLK MP3 player 1 GB flash memory and USB drive with LCD, high-contrast LCD display with 7-color backlight, plays MP3 and WMA digital music files, ID3 tag support for song information display, mobile data storage function, convenient integrated USB plug( no cables required), USB 2.0 hi-speed for fast file transfers, black.
Well problem seems in the file format of the mp3 player, please let me know in which file format do you copy the songs into your mp3 player? make sure the file format is supported by your mp3 player. (when you play these files in windows media player it played because window media player played all(maximum) file formats.) post further comments for more information....