"Lost" files and wont play music

First, iTunes stopped playing music. I double clicked a song, it would show up in the bar at the top, and then start scanning through all 14k songs in my library maybe playing every other song's first second or two. Then it started telling me that song files couldn't be found. Now it's doing both. I just upgraded to the new iTunes and it's still not working.

Further, I can't get the grey box to go away asking me if I want to search for the next song that's suddenly missing.

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