ITunes says my iPod is synced but songs are not appearing.

Question

I had to start all over with my iPod because all of my files were erased. I downloaded a bunch of new songs and videos and when I sync my iPod, a message appears saying that three of the files cannot be copied. I used to get that before too, so no big deal. But when I look on my iPod, the songs are not there. It is not telling me that it cannot be synced and the bar at the bottom of the preferences page or w/e says that I have 1.60 GB of music, 795.1 MB of video, and 25.42 MB of 'other'. I have already authorized this computer. Why won't it sync properly?

Answer 1

iTunes can "sync" an iPod, and not transfer any songs.  You may need to set up or update automatic syncing in iTunes for the iPod.  Otherwise, syncing may sync nothing.
First, if the iTunes sidebar (along left side of window) is hidden, from the menu bar, under View, select Show Sidebar.  When connected, the iPod appears in the sidebar, under DEVICES. 
Second, when you set up automatic syncing, the iPod's existing content is replaced.  Any songs on the iPod that are not in your iTunes library will be lost.  Is that OK?  If that's a problem, please post back.
Select the iPod in the iTunes sidebar.  To the right, the iPod's Summary screen is shown.  Toward the top, there is a bar of buttons starting with Summary.  Click on Music next to Summary.  This Music screen is where you tell iTunes how to sync songs to the iPod.
Check the box for Sync Music.  This setting enables automatic syncing.  If your iTunes music library can fit on the iPod, you can choose to sync Entire music library.  Then, "everything" (that is music) syncs to the iPod when you click Apply.  Going forward, any changes to the music library sync automatically to the iPod, at the next opportunity.
Otherwise, you can choose to sync Selected playlist, artists, albums, and genres.  Then, select (checkmark) what you want on the iPod from the lists below.  For example, you can have playlists in your iTunes library with songs you want on the iPod.  On the iPod's Music screen, select those playlists under Playlists.  When you click Apply, the songs in your selections sync to the iPod.  Going forward, to update your iPod, update those playlists in your iTunes library (add/remove songs).  The iPod does not need to be connected.  The next time the iPod is connected (or when you click Sync if already connected), iTunes updates the iPod with the same changes automatically.