I've run across this as well and it's actually a setting in Windows Media Player. The only way I've found to correct it (since I couldn't find it in the advanced options) was to start Windows Media Player and go to the sync page. Then connect the player to the computer. When Media Player recognizes the device it will pop up a screen (make sure you're in the sync page first) that says Windows Media Player - Device Setup. There will be two options, 1 to leave existing files and sync to remaining space and 2 to delete files before sync. Choose the first option to leave existing files and then click next and then finish. You should be able to sync new songs to the player now without it deleting the existing songs that are already on there.
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