I just want to update this topic to reflect what may have been a change with respect to the way Apple administers Match. Despite the fact that iTunes Match is proposed as a workaround for those of us with old DRM-protected content in our libraries — I found similar recommendations on a USA Today page, a Wired magazine guide and on the Macworld website — in my experience iTunes Match does NOT allow for m4a replacements as a solution for those of us who still have a lot of m4p's in our music libraries.
The Matches will indeed show "Purchased" but when you do a "get info" on the file it will still have an mp4 extension on it! So if you happened to have made a lot of purchases prior to 2009, which is the year Apple stopped using that particular kind of DRM, the DRM protection you ended up with back then will remain in place after using iTunes Match.
What's odd is that initially iTunes Match appeared to provide m4as but upon subsequent launches of the iTunes app I find they have rreverted back to m4ps. When sorted by "kind" the Matches continue to misleadingly state that they are "Purchased" even though they in fact remained Protected. Within a few days and relaunches of the iTunes app, they will update back to "Protected" in the sort-by-kind field. This applies to any titles purchased before 2009 — so, in other words, back to square one.
I am out of options under iTunes 11 given that there are no further updates for my OS. But I would assume, since Match is a Cloud service, that Apple made an adjustment to the way Match operates after this workaround was widely reported as a solution to the m4p/DRM issues that some users are continuing to encounter.
I used an iPod Photo for over 10 years and never gave a second thought to what type of file restrictions were in place. When you purchase your music legally, as I did, and do not attempt to stray outside the Apple fold, you don't realize the headaches you will encounter until it's too late. Back in 2009 when the DRM restrictions were lifted I never received any notice from Apple that it was recommended to upgrade to iTunes Plus or the like to make my 2009 and earlier purchases a bit more "future proof". I didn't encounter issues until I attempted to join the 21st Century and play my music library on a non-Apple smartphone. I quickly came to appreciate that many of the purchases I made in 2009 and earlier — because I've been buying through iTunes exclusively for over 10 years — could not be played back on anything but my ancient iPod Photo.
There are many website guides and many discussions suggesting that iTunes Match will provide replacements for DRM tracks, and at least initially it did give the appearance of succeeding. But in my library, at least, Apple has silently re-converted the Matches into what they were to begin — m4p's — and so I'm back to square one. I just thought I would post here to warn others that are late to these headaches that iTunes Match will only make things more complicated by first porting your library over to the Cloud and then, if you turn it off, having the outdated version on the Cloud come back down again once you turn Match back on. (With all the duplication headaches that implies.) When I found that my pre-2009 iTunes Matches were Purchases in name only, I attempted to re-match my library and now my housecleaning headaches have started over again. I've literally wasted hours.
As you can imagine, I cannot recommend iTunes Match. In the old days, if a particular software was updated you had to click "Agree" or install the update with some form of physical media. But with these Cloud based services there aren't update notices flashing across your screen to indicate that some functionality on the server (Cloud) side has been altered in some significant way. So it gives the appearance that your library has developed a "mind of its own" when it is entirely possible — probable, even — that there have been updates applied to the service that occurred behind the Cloud. Although there are menu options for turning the Cloud (Match) side "off", my observation suggests that Apple doesn't honor the "off" (do not tamper/modify) settings in iTunes 11. By all appearances, Match continued to modify my library contents every time I launched iTunes, even though I brought back down all my files to the local side for the sake of being able to sync my non iOS device. My take on the Cloud at this point is that it is very, very opaque to the user and yet functions like an open door — whereas the user of Cloud-enabled applications/services can't appreciate who is coming and going through that door. After experiencing these headaches I contacted Apple support. To even contact Apple support using their "Contact Us" form you have to type your name, email, etc. I asked for a refund — because I want Match to stop modifying my library even when I have it "Off" in the menu — and they said they could not help me because they could not locate my Apple ID, which was BS because the Support email contained my Apple ID-linked email and contact Info. Ugh.
