So we're going to hav to get creative with trouble shooting.
I'm guessing you have the iCloud Status column enabled; sort on that column to find all the tracks with a status of "waiting" or no status. Now, create a new folder on the desktop, highlight all the trouble songs in iTunes and drag-n-drop them into this folder. This is just so you have a backup of them and can refer to them.
Once that is done remove the trouble songs from the iTunes library, from the cloud, but keep the files. Turn off iTunes Match, wait about a minute, then turn it back on. Let it complete a scan.
Once the scan is complete start adding the troublesome songs back into the library a few at at time. After you add each small batch let iTM kick off and do its thing before adding the next small batch. It may be necessary to transcode some of the songs as well.