Itunes purchased music will not play on Ipod

I have had an Ipod since second generation around 2004. It lasted me until about two weeks ago and i recently bought a new fifth generation. When 7.0 came out my older ipod would not play my purchased music and suddenly started to give me errors(unhappy ipod, and folder). I took it into the genius bar and i was told that the hard drive had died. I think that is a load of hogwash. I was able to "revive" it to only have it die again. The new Ipod has the same problem with the purchased music. I have tried the 5 R's, I have reloaded my library, everything. I thought that possibly if the files were on a shared network it messed it up, but i have unshared everything. Nothing seems to work but reloading the purchased music from a cd that has been burned. I dont want to take the time to do that for over 350 songs. Are there any suggestions from a real Apple tech? And will this be SOLVED?
  Windows XP  

seems like Apple wants us to illegaly obtain the songs from now on. You know the story about starving musician, poor janitor at studio, well it is not important now.
I am done with being cool, now i want something that will actually work. lets see how long will it take for iTunes update to come accros, and will anyone in Apple say we are sorry guys, we screwed up. hmmm, maybe refund for all the songs you purchased would be fair, you know guys we sold you and told you it will work on your coputer, but look surprise they dont. no, not even crappy explanation, just new update.

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