Forced to re-authorize every time I synch my iPod with my computer

For some reason, the songs I have purchased through the iTunes store fail to download to my iPod whenever I synch.
They will be on my iPod when I plug it in, but they are often missing after the synch. The only way I have found around it is to select a purchased file. It always asks me to re-enter my password, yet the number of authorized devices remains at two (my computer and my iPod), even though I have to do this over and over and over again.
Isn't there a way to have these items permanently available to my iPod? Several times, I have forgotten to check purchased files, and I've ended up stranded on long trips without the audiobooks I had purchased and downloaded to my computer.

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