I don't have iTunes Match, and the problem for the songs purchased from Itunes was unselecting the allow multiple downloads in the downloads window.
I still have the problem when transfer mp3 songs to itunes, I fixed that make changes in properties of that song I just changed OPENS WITH: from Windos to ITUNES. Then open the song direct form the location and will open with ITUNES complete. The problem is cus need be one by one/
I use a similar playlist to find matched tracks that were corrupted while downloading. The only different setting on mine is I have Kind set to is "AAC audio file".
Downloaded matched tracks should take the "Matched AAC audio file" kind. In my experience those that download but have a kind of "AAC audio file" usually do not play correctly. I've been able to delete the local file and redownload the matched track and get a good file.
I also recently had a couple tracks which could not convert to 128kbps while syncing to my iPhone. These tracks were not showing up on my corrupt files playlist and they actually played fine on my Mac. I did the same and deleted the local file and redownloaded and the sync worked after that.