18 songs don't sync... rather odd I must say.

I have 2988 songs in iTunes but only 2970 will sync to my iPod. Somestimes it will give me an error that says soemthing like "iTunes couldn't sync all songs because your iPod software isn't up to date but when I go to update the software it says it's the most recent. Other times there won't even be an error.
please help.
thank you.
Eric

This is a regular playlist. I have no issue finding the song in the artist menu on my iPod. It's on the iPod, it's just not carrying over to the playlist that I made.
I have not tried restoring it yet. I was afraid that if I restored it I'd have to manually select which artists I wanted on my iPod again. It's a 60Gb iPod and I have about 180Gb worth of music so whittling it down to the 60 I wanted most was a laborious task. If I restore it do you know if I'll have to go through that again?
The reason why I think this must be an iTunes problem is because the latest update fixed this issue for my iPhone but not for my iPod. If it were an issue with sort values etc. I don't see why my iPhone would start working properly after an iTunes update.
I have tried making the playlist over again using a different name but the same songs keep getting cut from the playlist.

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Yeah, they worked in iTunes, I double checked that. In fact I found out because I tried playing some songs in my car and thought, hey, they worked fine on iTunes earlier today.
However, I ended up restoring it back to default settings through iTunes and letting it sync everything back up again, and it worked. 0.o Which is odd, since only a few songs didn't work, and I didn't change anything, but meh, this is technology. If it works, don't ask questions, just accept it.
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18 songs don't sync... rather odd I must say.

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