How much luck have you had with your own burned CDs library? I either get not matched or at best 1/2 an album.
I've slowly been doing one album at a time, and even stuff purchased from the store(pre 2009) with the same appleID will not not match whole albums me. It is very annoying to have one or two songs per album not matched and sill DRM locked.
Not to mention a number of my old purchases are not in the store anymore and I'm totally stuck with the DRM versions.
I talked to a Sr.Apple Care specialist and was told that's not the purpose of itunesMatch(remove DRM), just deal with it, and the things you read online are false. At least they said they would refund a prorated amount.
I personally think it is doing it on purpose just to mess with me. Literally every other album I try(ripped by me which is @128, or purchased from the iTunes store with DRM ) I get 1 or 2 songs per album that do not match.
One other thing I do not understand even if it does not match, it can certainly find it when I click "Show in store".
Do they still offer the $.30 upgrade for DRM'd tunes so I can match the stragglers?