Audiobooks going into "Other" folder when syncing on 5th gen video ipod

Suddenly a bunch of audiobooks I bought recently are not syncing properly. They seem to be going into the "other" category because when I look at my iPod memory summary, the colored bar chart, I see that category (in orange) growing but Audio (blue) remains the same. The files appear to be on the iPod when I look in iTunes but when I unplug the iPod and check there I can't find the audiobooks on the device. I restored twice, and then started getting the -48 error message. It seems as though iTunes is somehow misallocating the files and making them invisible. Any ideas how to fix this?
MacBook   Mac OS X (10.4.9)  

When you connect the iPod to any kind of powersource, or anytime you turn it on, it has these fans inside of it that start turning and shifting into place to cool the iPod off to keep it at a temperature at which it is able to operate. Soemtimes, the hardrive clicks as it does this to rev up, which is normal, like an airplane does as it takes off. On the other hand, if it does this non-stop for an extended period of time, then you might want to get it looked at by an apple genius at an apple store.
Dell Desktop   Windows XP   slllllllllooooooooooooowwwwwww

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