Ripped music will have the same benefits as music purchased from iTunes. Like it has already been mentioned, songs that are matched by iTunes will be added to your account and appear as purchased songs and will be able to sync to your other devices.
Songs in your library that are not in the iTunes catalog will be uploaded to the cloud, and then you can also sync to your other devices. That includes live recordings, songs created by you, etc.
Some of the benefits of iTunes Match are, upgrade lower quality songs to 256kbps AAC DRM-free songs, fix/add missing ID3 tags, fix/add missing album artwork, legitimize "pirated" songs or adquired elsewhere. Not a bad deal for $24.99 a year, specially for those with large music libraries. Like you, pretty much all my songs came from other sources. I've only purchased one (1) song from iTunes, and that's because I couldn't find it anywhere else at the time. The only other music I've gotten from iTunes are podcast mixes which were free and there are plenty of them in the iTunes Store.
Oh yeah, once you cancel iTunes Match, you still keep those songs, as they will be treated as purchased songs.
I guess that's why Apple payed a hefty sum to the record labels to make all this happen.
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