Ipod wont update songs from itunes after new update

I downloaded the new itunes update 5.0 and now i cant update my ipod. it keeps telling me that there is not enough room on it. so i unchecked about 1000 songs and it keeps on saying the same thing. it also took about 3000 songs off my ipod. the only way it will update is if i let itunes update it with a choice of songs they pick. please help.

Hello All,
I think I came up with a work around by accident and didn't realize it until I read this post.
Did all the same stuff most have done, reset to factory, reapplied the updates, etc, still not enough free space, even though there was plenty before.
Sooo, I went into iPod options, changed from "Automatically update all songs and playlists" to "Automatically update selected playlists only". I did this assuming that the amount of space used on my iPod would be cut in half, at least. So I sync'd and when it was done, my iPod was back to the way it originally was, having about 800MB free on a 30GB G3 iPod. Hmmm... so I looked at the pref's again and realized that the "Only update checked songs" was still checked. I have been using this setting for at least the past two years after my audio collection began to exceed my 30GB iPod's capacity. So in the end, it ended up syncing just my playlists PLUS anything that was checked which brought me back to where I started before I made the jump from 4.9 to 6.0.1. The only difference was the switching the setting "Automatically update all songs and playlists" to "Automatically update selected playlists only". Very odd. I suspect a lot of users got in trouble on this one.
Please let me know if this fixes the problem for anyone else.
Kindly,
James

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