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Most likely why that isn't working correctly is because your usb port on your computer is most likely bad... I know someone who had the same problem and once she plugged the player into another usb port it worked like a charm.
You probably noticed that the directions for deleting in the manual simply don't work, the option isn't there. There are still a couple ways to do it.
Connect the player to your computer, navigate to the device and select the files you wish to delete, then press delete. Somewhat time consuming if you have a lot of files.
Another way is use Windows Media Player to sync the device. Load your library with the files you want on your player, then sync. WMP will delete all files on the player now, and put only the files you have selected on the player.