IPod Classic will not properly sync

Question

Hey everybody. I'm really hoping that somebody could help me out with this, as I am getting rather frustrated with it.
My iPod Classic 120GB will not properly sync with iTunes on Windows 7. When I plug my iPod into my computer, I get the typical "Scan & Fix" message from Windows, and I generally just close the window without selecting an option (to Scan & Fix or Ignore), as neither option has ever seemed to change anything.
I used to have over 100GB of music on my iPod, collected from various sources over the past 5 years or so, but a few months ago I plugged my iPod in to add new music to it, and iTunes did not recognize any of the files on my iPod. When I ejected it, there was no music on my iPod, but it still had 100GB of space filled. I decided to just bite the bullet and reformat my iPod, even though I would be losing most of my music, in hopes that I could make it work correctly.
However, after I reformatted it, I have continued to have problems. I have reformatted using both iTunes and the Windows reformatting tool. Every time I plug my iPod in to add new music, the same things happen. I'm not automatically syncing iTunes to my iPod, because I like to be able to manage my music manually. I can add some music to it, but certain files will not copy and then nothing alphabetically after those files will copy either. I eject my iPod and use it normally throughout the day, but then when I plug it back into my computer again to try to add the rest of my music, iTunes says that my iPod has no music on it (even though space is being used). When this happens, I just restore the iPod and try again, and this is getting extremely aggravating.
My music is all in MP3 format, and I am not trying to add movies, pictures, or any other files to my iPod (other than cover art). I have run anti-virus checks and stuff on all of my music files, and everything has come up clean. Should I try converting all of my music to AAC, or will this just take forever and not actually fix anything? I have already tried downgrading to an older version of iTunes, and I have still been having the same issues. I don't know what else I could do, and I really don't have the money to buy a new iPod.
Thanks in advance for any help or advice!

Answer 1

There may be some hardware fault on the iPod's hard drive, which is causing this problem.  Your use of manual loading may be agravating the problem, because you are making the iPod apply many small incremental disk access updates.  If you used automatic syncing, iTunes makes all changes at once, with one disk access, then dismounts the iPod's disk and spins down until the next sync, when it again makes all updates at once.
I understand why you want to use the manual method, but here's a way to "replicate" what you do manually using automatic syncing.
Create a new playlist in iTunes.  Load this playlist with ALL the songs you want on the iPod. 
Select the iPod in iTunes.  There is a row of "tabs" (starting with Summary).  Click on Music there.  On the Music tab, set it to Sync music using Selected playlists, artists, albums, and genres.  Below that, keep it simple by checkmarking ONLY that new playlist with the songs you want on the iPod.  When you click Apply, the songs on that playlist sync to the iPod.
Going forward, to update the iPod's songs, just update that playlist (add and remove songs).  Basically, instead of manually updating the iPod, you are manually updating the playlist.  It's the same work, but with several key advantages:
- The iPod does not need to be connected to make updates, increasing flexibility and reducing wear-and-tear on iPod.  Just connect the iPod once after you are done making all changes to the playlist.
- Updates to a playlist are instantaneous.  Updates made directly to an iPod (especially one with a hard drive that may need to spin up) takes a few seconds to a few minutes, depending on data size.  You're just waiting.
- Many small updates to the iPod's hard drive is more wear-and-tear, compared to iTunes applying all of your changes with one consolidated disk access.
- iTunes keeps the iPod's "disk" NOT mounted, except when syncing.  This reduces wear-and-tear, and the chance of data corruption occuring.  The manual method requires the iPod's disk to be mounted at all times (until ejected).
- Because the iPod's disk is not mounted most of the time, you don't need to eject before disconnecting.
- You have a backup of all of your iPod songs on the computer's hard drive.
- If you do a Restore, or if you get a new iPod, all you do is go to the Music tab and select that one playlist again, and click Apply.  Everything back to the way it was before, with a few mouse clicks (and 20-30 minutes or so of syncing).
If you want multiple playlists on the iPod, just create those playlists in the iTunes library.  Name them so that they all appear grouped together in the iTunes sidebar.  Checkmark those playlists on the Music tab.  Do your "song maintenance" in iTunes using those playlists, and let iTunes automatically sync all changes at once the next time you connect the iPod (or click the Sync button).
Try setting it up to use automatic syncing, to see if there is any improvement.