Strange Itunes Mystery

Okay here's a goody to figure out.
First some details.
I live the the U.S.
I have a Mac OS X, 10.6.8 (2008) 2.4 GHz intel Core 2 Duo
I'm running the Snow Leopard OS.
I have recently done all the software updates sent by Apple. This included a recent update for Itunes
I downloaded Rubber Soul by the Beatles from Itunes.
All the songs successfully downloaded onto the Mac
When I hooked my Ipod classic up to get the new songs onto the device, the computer told me it could not download the the song "Wait" because it could not convert the file. 
I went to play the song on the mac and a screen pops up and tells me the computer is not authorized to play the song. I go through the authorization process and the computer tells me it is already authorized but when I go to play it will again tell me it is not authorized.
I deleted the song. I went to the "Purchased" section of my itunes account to try and re-download the song. I could find the song but Itunes gives me no option to reload the song. I have only used 3 of the 5 locations that Itunes will allow to keep downloads.
I go back into my Mac to fish the song back out of the trash.
With Finder I locate the file and drag it back to Itunes and put it back in the system. It still will not play.
I go to the file over in Finder and there is a gif in the little cover flow section at the top of the window. When I pass mouse over the pic a little play button appears.... incredibly enough the song plays when I hit the button.  Apparently, while accessing the file in Finder and not Itunes the song plays. 
So what I don't understand is why this one song not working in Itunes. I have a lot of music on my mac (almost 90 GB). As far as I can tell this is not happening anywhere else in the whole of my library. I've done a lot of downloading from Itunes and I've had glitches before, but Itunes and the Mac have always been able to correct the problem pretty simply.
Thanks for any help.

When you run network diagnostics and anything fails, there is a help button that should come up to help troubleshoot what might be blocking itunes.
Try turning off any internet security, firewall or anti-malware that you might have running on the computer. If this works, then check the website for the programs you turned off and see if there are any updates.
Here is an article from the apple support website that might help out.
http://docs.info.apple.com/article.html?artnum=302538

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