I have a big mess-most of my files in purchased tab have exclamation point

Most of my files in purchase tab have exclamation point and will not play. However they are in my library and I can play. Most files in my library are duplicate or even triplicate and at least one of the duplicates has an exclamation point. Also seems that my ipod is trying to sync doubles...causing memory size problems.
I have recently consoladated files to an external drive following apple's instructions however think that this has contributed.
Please help.

Hi, TBJAPAN.
Why don't you try deleting the extra entries in the iTunes display and see where that leaves you.
MacMuse has a user tip you may find useful in this regard.

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