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Are you running the most current version of iTunes? If not try upgrading. After that, try seeing if there is an firmware upgrade. If there is, try upgrading that too. Then try reuploading songs. If it is still not working, it might be damaged or just not working anymore. Only use Itunes when uploading songs to ipod regardless of type.
When you sync, you are telling Windows Media player to make the player match what is currently in your sync list. So if you removed the first 110 from your Windows Media, that is why they disappeared from the player.
You don't need to use Windows Media player to add songs. Simply open Windows explorer, double-click your Sandisk device, double click the music folder, then drag and drop any files you want into the folder.
If you clicked "yes" to an Update for your device, then all your songs have been wiped. Firmware Upgrades and Repairs (whether performed knowingly or unknowingly), will delete all songs from your GoGear.
Alternatively, when you have automatic synchronization set up for Windows Media Player, then re-syncing to the device when the songs don't exist on your computer will also cause the GoGear to be wiped. It's a feature of WMP that I don't like.
I think that the problem is with the songs file formats.
Try checking that they are all mp3. if they aren't then you have to convert them using an "MP3 Converter" software. there all plenty on the web.