Originally Posted by Sam Posten
iTunes Match has possibilities, I wonder if it will let me convert the $1000 I have in DRM wrapped iTunes tracks to cloud based free downloads as part of the $25
Sam, from my reading of the description that's exactly the case, assuming they still have those tracks currently available in iTunes. Not only will you have access to DRM-free versions, they'll be 256 kbps instead of the 128 kpbs you probably purchased them at.
Edit: Hmm, maybe not. From Apple's "iTunes in the Cloud" page:
If you want all the benefits of iTunes in the Cloud for music you haven’t purchased from iTunes, iTunes Match is the perfect solution.
But apparently the new Purchase History / Download to all of your Devices feature is available in "beta" today, by downloading iTunes 10.3. It will be interesting to see if your older tracks show up there as accessable in DRM-free versions.