My computer wants me to authorize even though it's authorized; can't play my music

I'm using a mac mini with Lion 7.1. Suddenly, tunes I've been playing for years won't play. They say to authorize my computer, I authorize it and they still won't play. It's not all songs, just some I bought years ago. Songs before and after play fine.
HELP.

And now, the Apple Support person who said he was going to call me, didn't. He won't return my emails. I'm out a couple of hundred dollars of purchased music I was able to play until recently.
I've authorized, unauthorized … sent in every computer serial number I used to purchase music and the music gets stuck in a loop that asks me to authorize something that's already authorized. This is obviously an Apple CRM nightmare that iTunes simply refuses to fix.
I also have hours of my valuable time gone dealing with Apple's mess. I really need help and Apple is turning a blind eye.
Why would I ever buy any music from iTunes again? I've never had this issue with Amazon or CD Baby.
Can someone help me, or will I just get ignored.

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Michael,
Thanks. I haven't mixed down the audio or checked the number of tracks in Prefs. Good points.
As far as a mixdown goes, I'll definitely give it a try, though I wonder whether or not the tracks will be recognized during mix down recording - given that you can't hear either of those segments in playback. Just have to try.
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Possibly nobody has answered this in 10 hours because your question is not clear. Accept? What exactly are you trying to do?
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iTunes application window (not Finder or a browser) > menus at top > Store menu > drag down to Authorize This Computer. (In earlier versions of iTunes access this option from the Advanced menu). Step-by-step instructions - https://discussions.apple.com/message/16569470
Image of where this is in iTunes 11: https://discussions.apple.com/message/20585561

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The cable would be much cheaper than the Scotch!
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Hey CarlyR_,
Thanks for the question. I understand you are experiencing issues related to iTunes Store authorization. The following resources may help to resolve these issues:
iTunes repeatedly prompts to authorize computer to play iTunes Store purchases
http://support.apple.com/kb/TS1389
iTunes: Missing folder or incorrect permissions may prevent authorization
http://support.apple.com/kb/TS1277
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My computer wants me to authorize even though it's authorized; can't play my music

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