Music Loaded but Won't Play

I have a 160GB iPod and a lot of music on iTunes (approximately 31,000 tracks using 147GBs). The music comes from several sources -- iTunes purchases, CD rips, e-Music, Amazon.com, and other downloads. My problem is that when I sync the iPod (attempting to load all my music on it) and eject it, the iPod indicates that it is holding only a portion of the music in iTunes (e.g., 23,274 tracks) and won't play any of them. When I try to use Coverflow on the iPod, it doesn't respond. If I hit play on the Artist or Album list the iPod reads No Artist/Album. The Search feature is unable to locate any tracks on the iPod. If I try to load only a portion of my music (e.g., all music by bands whose names begin with the letters A through O), I can load and play the music on the iPod. Of course this isn't why I bought the 160GB iPod -- I wanted to load all my music. I have tried this with 4 new 160GB iPods with the same results. So I spent a considerable amount of time trying to clean up my music files by converting them to AAC hoping this would correct any conflicts or corrupted files. It doesn't seem to have helped and no one at Apple Support has any ideas. Has anyone experienced this problem or have suggestions?

Well, my first thought is your iPod is full. Remember, though it is called a 160GB iPod, this means 160 billion bytes. This translates to approximately 149GB (as computed by the iPod or any other computer). If you account for overhead such as album art, games, operating system, library database, etc., the iPod may just be filling up prior to completion. I do not know what happens in such a case.
And the reason for the discrepancy - hard drive manufacturers use Base10 when marketing their wares; computers (PCs, Macs, whatever) use Base2 when computing drive size (or memory size, for that matter). So, 160 billion is (10^9)*160. However, the computer computes 160GB as (2^30)*160 (or a little over 171 billion bytes). Designating GB as 1 billion bytes has been standard marketing for the past 20 years.

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