Burned and purchased songs won't play in iTunes

My wife got a new computer.  Really nice rig.  Runs Windows 7.  And with that a new iTunes installation (she never installed the new one.  she doesn't like change).  All the songs she burned from CDs, and I was just informed all the songs she's bought, show up in iTunes, but won't play (I imported ALOT of stuff from an external HD onto the new computer).  The music files still exist in the iTunes music folder.  She can even play the song if she manually clicks on the file in that folder.  But try to play the same song through iTunes and no luck.  It's rather frustrating for her.  And this kind of stuff doesn't exactly endear me to iTunes stuff either (and don't get me started on GameCenter on my iPhone).
Anyone know what's causing this issue and how to fix it?
Thanks.

The folder you see as My Music is really called Music. Windows will present such special folders with different names depending on the context, so the same folder on my computer when viewed from another user's account would show up as Steve's Music.
What we haven't established yet is the layout of the (original) media folder which is why I suggested the other route first followed by a clean up, however I was going to recommend that you rearranged things into the standard layout and from what I can see there is no reason why it shouldn't work if you just put things where they are expected to be right now.
Here are the typical layouts for the iTunes folders:
Note that in the newer layout all artist folders go into a Music subfolder within the media folder.
If you move everything that is currently inside iTunes Music into iTunes Media, including the hidden file iTunes Preferences.plist, iTunes should pick it all up without further problems.
Once iTunes is in touch with the media if the artist folders are at the level of iTunes Media rather than iTunes Media\Music use the option File > Library > Organize Library... > Rearrange files in the folder "iTunes Media".
tt2

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