I think what you want to do is in your music program for your mp3 player, set the default directory for your music library to somewhere on your external drive--that way all the songs will be on the external drive and you need not worry about having them take up space on your Windows drive if you're running out of space. Just make sure to copy/paste your old music directory to the new one--so that all of your songs are transferred to your external drive. Without knowing the player or software I can't really say more than that.
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