Can I--should I--combine the newer iTunes Media folder--new since 10.5.1--and the older iTunes Music folder? I just realized all my new songs are going into the Media folder, and I kind of like the simplicity of everything being in one, not two, folders.

Most of my music--the VAST majority--is in iTunes Music, but all the new songs are going into iTunes Media, which is new, I think, since 10.5.1.

The missing file thing happens if the file is no longer where iTunes expects to find it. Possible causes are that you or some third party tool has moved, renamed or deleted the file, or that the drive it lives on has had a change of drive letter. It is also possible that iTunes has changed from expecting the files to be in the pre-iTunes 9 layout to post-iTunes 9 layout,or vice-versa, and so is looking in slightly the wrong place.
At guess you've used a different profile name. Files inside the media folder have survied the transfer, but those outside are expected to be on the same absolute file paths, but no longer are.
Select a track with an exclamation mark, use Ctrl-I to get info, then cancel when asked to try to locate the track. Look on the summary tab for the location that iTunes thinks the file should be. Now take a look around your hard drive(s). Hopefully you can locate the track in question. If a section of your library has simply been moved, or a drive letter has changed, it should be possible to reverse the actions.
Alternatively, as long as you can find a location holding the missing files, then you should be able to use my FindTracks script to reconnect them to iTunes.
tt2

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