Unusual syncing problem with ipod Classic

I recently bought a new 160 Gb ipod Classic and the first one that came seemed to sync all my music but as soon as I removed the cable I got an Apple screen and an unresponsive ipod. Eventually Apple swapped it for a second ipod. I found it difficult to get this one to work properly although the hard disk on this one hadn't failed like the first one.
I did have to restore the new ipod at least twice and after the second time I decided not to sync all my music at once as before but selected a few genres to start with and it worked fine so I gradually selected more and more genres each time I synced it until I had all my music on the ipod. So all was fine.
After using the ipod for a couple of weeks or so with this I decided to try and sync the ipod by selecting All the music rather than by genre. As all the music was already on the ipod this didn't take very long to sync. As I normally play the music on random shuffle I selected shuffle and what happened next I've never seen before but the track that was about to be played appeared on the screen but didn't start playing. As I pressed the play button the track wouldn't play but the ipod jumped to the start of the next track and just kept doing that without playing anything.
I then stopped this and decided to sync the ipod as before by selecting all the genres. When this was done the ipod then played normally as before. While this is fine I'd like to be able to sync my ipod by selecting all the music as I've been doing for years with my old ipod Classic 80 Gb. Is there anyone who can explain what might be causing this problem to occur?

Ok here goes, after 6 weeks of restoring, resetting, putting device into manual scan, manually resetting, downloading itunes older versions, newer versions and all around fighting my ipod; I have had the same results. When restoring through itunes the ipod is "still named", now one would think when doing a full system restore on the ipod via itunes it would do a full restore and the name would be no longer existent, so not the case. I have gotten multiple error messages, this is the most prevalent, "The "ipod name" cannot be synced. A duplicate file name was specified", another is in order for this ipod to work you must restore with itunes. I am thinking that there is problem with the new software, you see yesterday I set up a computer that has XP and itunes 7, the sync went without a hitch, no freezes, no long pauses, no problems. Then I made the mistake of hitting the button to update itunes "newer version", rediculous mistake. All of the problems are as pevalent as before, ipod will not sync, manually I can add movies and music but no more than 264 songs will add. My question is, why did Apple create this very nice, durable large player if they do not have the capability to serve they customers with the correct software?

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