For $25 a year Tunes Match allows you to easily listen to any music from your iTunes library on any of your Apple devices or computers running iTunes. Music from iTunes Match can be downloaded or streamed directly from Apple’s servers. Competing services like Google and Amazon make you upload all of your music to get it into the cloud. iTunes Match instead scans your iTunes Library and compares your tracks with the iTunes Store's catalog. If it can match a song in your library with a track from the iTunes Store’s 20 million song catalog, iTunes Match doesn't bother uploading the music file and makes it instantly available for downloading and streaming as a 256kbps AAC audio file. If a song is not available in the iTunes Store, it will be uploaded and made available for downloading and streaming in its original file format. Neither matched tracks nor uploaded songs count against the 5GBs of storage that iCloud provides to every user, and every song matched in iTunes can be download again DRM free.

For geeks iTunes Match is a great way of upgrading your existing music collection. For a single one time fee Apple will match up to 25,000 songs of existing music and allow you to replace those tracks with pristine DRM free 256kpbs AAC audio files. For normal people iTunes Match will solve the problem of getting the music they have on one computer to all of their computers and Apple devices without networking, filesystems, or sync cables. For me iTunes Match is a frivolous expense. Most of my music comes from the iTunes Store already, and the tracks that don’t have already been ripped from my collection of CDs in DRM free 256kpbs AAC audio format. The only advantage iTunes Match provides me is the flexibility of streaming or downloading songs on the go when I am away from my computer. (I already know how to transfer my iTunes Library to multiple machines.) Until I can think of a reason not too, I am going to keep my $25 a year, and save iTunes Match for the people who need its synchronization services or generous upgrade in quality.

Update:

Jason Snell shows you how to use a Smart Playlist to quickly identify which songs would benefit from a upgrade to iTunes Match.

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Make a Smart Playlist Create a Smart Playlist with the following attributes:

• Bit Rate is less than 256kbps
• Media Kind is Music
• Any of the following are true: (to create this conditional, option-click on the plus button in the Smart Playlist window) iCloud status is Matched, iCloud status is Purchased

This creates a list of all your low-bit-rate files that are upgradeable—namely, ones iTunes Match has deemed Matched or Purchased.

Once this list is created you can delete every song it contains and download upgraded versions in glorious DRM free 256kbps AAC audio format.

If I was Jason Snell I could go one step further and add "Kind is not 'AAC audio file'" to my list of smart playlist conditions because AAC has better compression that competing audio formats like MP3.