You have to sync them at the same time in order for them to stay on there, or you can do it the easy way and go to the ipod's main menu and click on manage your files and after you do that, you will be able to click and drag everything you want onto there.
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I know another way you could try formatting which may fix this problem. Restoreing just restores all the setting to your iPod yes it shoudl format as well but it may not due to an error or something.
To do try it another way follow these steps, first click on "Start" - "My Computer" look for you iPod when it's connect usually called "Removable Disk" once you've found it "Right-click" on it then click on "Format", once format is complete disconnect, then connect it again then run "Update" for your iPod and for iTunes, once you've done that have another attempt.
Good luck. Hope my solution was helpful in some way. Further problems leave a comment and i will get back to you.