Random songs in library won't sync to iPod

I can't seem to find anything on this so I thought I would throw it out there...I have my iTunes library on a 250 Seagate external HDD. About two weeks ago, I connected my iPod to sync it (5th Gen 60GB)and iTunes couldn't seem to find the new songs. I manually told iTune where they were, resynced, and then it couldn't find a much larger selection of the library that was different from the first. I removed the library, started over and everything seemed fine until I connected the iPod and the same thing happened. I can't seem to get the entire library onto the iPod. There's enough room on the iPod to hold the entire library. I'm not sure if it iTunes, the iPod or the HDD. I purchased another external harddrive (since I needed to back up anyway) and the same thing happened with the new HDD (WD 350). Any ideas?

I have noticed that it seems to be a bit rate size problem. My iPhone only adds songs or vids less than 127bps. Now, it's possible that it could be slightly higher, but that seems to be the limit of the stuff I have. Nothing 158bps or 160bps or 192bps or 256bps syncs over, though it did last week! Is it possible this limit was inadvertently imposed in the last update? Problem only appeared after last iTunes update. Could have been with 3.0 update but I don't think so. However I have noticed when they do sync, after I play them or partially play them they disappear from the playlist on the iPhone, should I go to another app and them come back to it.
I don't want to reduce the bit rate, I want iTunes to fix itself, gol-darnit!
Anyone know of a solution or heard of this?
~Deb

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Random songs in library won't sync to iPod

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