Can I get iTunes to show all songs with an error status?
You can add the columns iCloud Status and iCloud Download and sort song lists by those criteria.

All songs that didn't upload will include the missing tracks so you can clean them appropriately.



You could also attack the inverse problem. Make sure everything you care about is in the iCloud and matched. Once that process is complete, you could turn off iTunes Match on that computer, quit iTunes and archive the entire music folder. Then you could delete the library folder and start with a fresh library and turn on match to restore all playlists, metadata, play counts, etc...

At that point, you could decide to re-import some or all of the songs so you don't need to download all the music again, but most with broadband are happy to just re-download what they need rather than have everything in one place.

I have done this exact process, and when I go to iTunes and select a track I want to delete, the following dialog pops up:



If you are not getting that dialog, then I can only presume some other corruption is present in your Library.