Files in library but won't import to ipod

I have @8200 songs in my itunes library. When I hooked up my new 60G ipod files transfered fine, although my ipod says I have 8194 songs, it is only using up 28G of space (it is using 42G in my library). I found out why. I went to play some songs on my ipod today and it just scans through all of the tracks on the album and then defaults back to the menu. Some songs play...some don't. When I right click on the song in my library and click get info, it has the right directory address and everything. All the songs play fine in my library, just not on my ipod. All of the songs are listed on my ipod, they just won't play. I have tried updating over and over. I have reloaded itunes software. I have tried consolidating library...nothing works. Any suggestions please?

If the skipping songs are purchased iTMS music, then make sure that you have the latest versions of iTunes and the iPod firmware installed. Then authorize the songs by playing one of them for a few seconds.
If the songs are all imported AAC or MP3 files, then it may be an iPod memory management issue.
Restore Your iPod and reload the music back onto the iPod, from your iTunes.
If the Restore & Reload does not work, see: “Strange iPod Behavior within Windows”

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I was thinking about why the songs arent importing and I feel that its either, A) the format of the files has changed since you last imported them, or B) you may need to rebuild the iTunes library.
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Re-creating the iTunes Library file
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1. Quit iTunes.
2. Locate your iTunes folder (this is the folder that contains the iTunes Library and iTunes Library.xml files).
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/Users/[your username]/Music
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\Documents and Settings\[your username]\My Documents\My Music\
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\Users\[your username]\Music\
Microsoft Windows 7
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3. Open your iTunes folder.
4. Drag the "iTunes Library.xml" or "iTunes Music Library.xml" file to the Desktop. If neither is available, learn how to add files back to the Library (because the XML file is not available, playlists and other information will not be available).
5. Drag the following file from your iTunes folder to the Trash:
Mac OS X
"iTunes Library" or "iTunes Library.itl"
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6. Open iTunes.
Important: Do not add any content into iTunes at this point (such as by purchasing something from the iTunes Store).
7. Choose File > Library > Import Playlist.
8. Navigate to the "iTunes Library.xml" file on the Desktop.
Mac users: Click Choose.
Windows users: Click Open.
If your Podcasts list in iTunes is empty after following these steps, learn how to add them back into iTunes.
Regards,
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Files in library but won't import to ipod

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