I was one of those suckers that paid $0.30 on every song to upgrade my entire music collection to DRM Free 256kbps AAC audio format using iTunes Plus. Now iTunes Match offers the same upgrade for one low payment of $25, and the best part is you don't have to resubscribe every year. Better yet, Serenity Caldwell, and Jason Snell of Macworld have found a way to upgrade your entire family for the same low price.

iTunes Match will upgrade any protected track authorized to play on your Mac even if that song was purchased with a different Apple ID. Have a family's worth of music sitting on your Mac's hard drive? No problem. As long as your Mac is authorized to play back those songs iTunes Match will allow you to download your family's matched music in DRM free 256kbps AAC audio format.

I imagine iTunes Match will be a huge hit in the college dorm scene. For one low price an entire dorm can upload all of their protected tracks, and up to 25,000 songs acquired elsewhere, to a single computer and authorize that music to be upgraded by iTunes Match. It does not matter where the music came from, or who purchased it as long as it is authorized to play. Once the music has been upgraded it can be distributed to the entire group. iTunes match does not make music sharing legal, but it does remove the obstacle of Apple's FairPlay DRM.