We don't know yet, but one probably will never "own" your iTunes Cloud data the same way you own your music now, I concede that. Still, you'll have access to all your pirated music as long as you keep paying 30 bucks a year.
It's actually a brillant move. Similar to being exempted from punishment if you turn yourself in as an owner of illegal guns/tax fraud or what have you.
They said the iTunes Match songs get downloaded as DRM-free AAC 256K files, so you will "own" it in the same way you currently "own" music purchases from the iTunes Store.
Perhaps, but if you committed copyright infringement when you originally obtained the music, none of this is going to turn back the clock and undo that original infringement