IPod skips over purchased music

I have a weird problem with my iPod, and I was hoping someone here could help me with it.
Every couple of weeks, my iPod goes through this weird stage. It will not play any of the songs I purchased from iTunes. I can click on them normally, but then it just skips over all of them instead of playing even one second. It plays all the songs from CDs and songs I had on my computer before just fine, but NONE of the songs I've purchased from iTunes.
Another weird part is that whenever I hook the iPod up to the computer, the problem goes away. But this doesn't help much, because I'm going to be away from my computer for most of the summer, and I would like a working iPod. Most of my files are from iTunes, too.
I know this is a really weird problem...I couldn't find anything on the apple FAQ, etc, so I'm sure it's not common. If anyone could help me with it, though, I would reallllllly appreciate it. Can anyone tell me why it does this, or (most importantly!!!!!!!) how to prevent it?

Welcome to Apple Discussions!
Make sure all the software on your computer and iPod is up to date...
iTunes
iPod Updater
Updating iPod's Software
Also, try the steps listed here...
http://docs.info.apple.com/article.html?artnum=303854
btabz

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