Purchased music skips after a few days

My iPod skips my iTunes' purchased music after a few days. When I connect my iPod to the iMac again the songs are back on my iPod but only for a couple of days.
Can some of you help me out to solve this problem?

The same thing happens to me, and unfortunately, it almost always seems to happen at the worst times (getting on a long plane flight.)
I've done a lot of research on this topic in the Apple Discussions groups, and have tried all the suggested remedies:
(1) Re-setting ipod
(2) Re-loading music
(3) Updating firmware, software
Net/net, when you update your iPod, and connect to iTunes, or do any of above, it will work for a little while, and then it will just start skipping purchased music again.
I believe this must be result of defective players, or bug in some of players, as not everyone has this problem (my wife's works fine) - but based on number of comments re. this problem I see on this forum, many people do, and Apple should offer exchange.

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