I just ran into an issue with using iTunes Match and having tunes that are ineligible. I have a list of songs that for one reason or another are not being uploaded to iTunes Match Cloud. I’m sure Apple has a list of reasons why songs may not be eligible, I’ve seen it. That list explains a few of the songs on my list but not all. So at first I wasn’t concerned. No big deal, who cares if they are in the Cloud or not right? Well, the issue came in when I wanted one of those songs on my iPad to use in class. iTunes will not let you put an ineligible song on your iTunes Match enabled iOS device.
This could be a huge issue. For instance, I have songs that I have recorded accompaniment tracks for the choir for, using my keyboard and laptop at home in my studio. Those are songs that I would obviously like to be able to have on my iPad so that when I am at school I can use them. For some reason some of these accompaniments that I have created are in that list of ineligible songs.
The solution I found was easy enough. I simply put those songs into a playlist, burned a CD of them, deleted them from my library, and then imported that CD of songs back into my library. Issue gone. You could get into a pickle though if you need a certain song FAST and it is on your ineligible list though so it would be a good idea to make a SmartPlaylist of all songs that are ineligible for iTunesMatch and check through so you know what all is on that list.
Good luck with your conversion to the Cloud… it will be a journey full of twists!