Ipod won't sync and some music disappeared from drives

I have about 2300 songs on my Ipod classic 30gb.
Recently I was asked to automatically update Ipod. At any rate, yesterday evening I noticed that there were a few exclamation marks on my playlist. It turns out that about 35 songs have suddenly disappeared off my hard drive. About 30 of them were all loaded around the same time (about 6 weeks ago), but not all the songs from that date were missing.
Now, when I go to sync, my Ipod will not sync with ITunes (I first tried because the deleted songs from my drive are still on the Ipod).
I am also seeing that my Ipod music is coming up greyed out. When I tried the diagnostic, I received what many have been writing about. A message that says "one or more sync tests failed."
Since I have the music on my computer, and own the music of the missing songs, I reset my Ipod and did a restore. The problem is NOT fixed. I will get the Ipod to sync when the music gets loaded back on, but then, never after that.
All the missing songs had been deleted from my Itunes playlist before doing the re-sync to make sure it was not a corruption issue.
Meanwhile, 2 other curious things. I have an older Ipod that does show up. But I also had a friend who brought her Ipod over about a month ago. We plugged it in and it was greyed out at the time. We couldn't access it on my computer. I didn't think anything of it at the time, but now I am concerned. But this was before I updated the software.
I will say that even before the update, I would get messages acting as if I did not have anything on my Ipod drive (it would say, no disk in Drive I, where the Ipod would be). This usually happened at the end of a session and I would
just hit continue or cancel and it would just go away. The bottom line was that it always synced for me. Now, after an alleged sync, it says it's syncing, but it doesn't really do it.
I have done extensive virus checking and my computer is not infected.
Numerous reports on not being able to sync have appeared on the internet and I have not seen 1 single solution, except for a fix on the IPod shuffle. This looks to be a potential ITunes update glitch.
My fear is buying a new IPod and having this thing happen again.
Essentially it ends the life of your IPod at the songs you already have stored on it. Unless I want to just keep restoring my Ipod every time I load music, which, to be honest, is ridiculous.
However, that is the only time this will sync.
Anybody know what I can do?

I just tried CopyTrans Doctor, based upon the suggestion on another thread.
I am glad it is a trial, because it said my IPod is fine. It is not fine.
Still trying to figure this one out.

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