Why is the music list for my ipod classic grayed out in itunes?

why is the music list for my ipod classic grayed out in itunes?

I have a similar problem.  Originally, my iTunes advanced setting was set such that a shortcut to the song was copied into my music library so sometimes copying songs to my iPod resulted in them being grayed out.  I changed that setting some time ago and haven't had the problem until recently.
I don't know what to do.  here's the situation:
     1.  I have a song that is stored on my file system within My Documents. (it was purchased via Amazon)
     2.  Through iTunes I choose the File | Import file to library (or some text like that)
     3.  I navigate to the location of the song
     4.  I import it.
     5.  I can play the tune from the music library or from an internal PC playlist.
     6.  I then attempt to copy the song to my iPod.  When I do, it appears in the iPod's playlist grayed out.
I have done those steps countless times for dozens of songs without a problem.  Even others that I've purchased through Amazon.  What is so different this time?  I should mention that this problem NEVER happens if I buy the song through the iTunes store.  Only if I buy it from another source (e.g. Amazon).  WHY ???

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