If you're interested in having your entire iTunes library in iCloud via the new iTunes Match service, check out the excellent tutorial on TiPb. It walks you through the process both via text and screen shots, and via a video. The process involves downloading iTunes 10.5.1, going into iTunes and signing up for the $24.99 service, and then initiating the service by clicking the option that says Add This Computer. This starts the matching process as iTunes goes through your library and matches your songs with the iTunes catalog.
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