I don't know about all this. I have a motherload of files on my HD (100+ GB of MP3's) but they're all ripped off CD's I or someone I know owns. Everything is indexed, categorized, and CLEAN. Why is this illegal?
You are legally entitled to be able to rip CDs that you own. Ripping a CD that "someone you know" owns is a different matter; you didn't pay for the disc, so in the view of the record companies, you shouldn't have those MP3s.
As far as how many reproductions of a CD
I own that ASCAP says I can have... ASCAP can f*cking suck it, for all I care. If I buy a CD, I will make 3486483276 copies of it in every damn format that I please, and unless I give out copies to other people, there isn't a damn thing they can do about it. I can have a copy of that CD in every room of my house, in each of my cars, and at my workplace, and as long as I'm the only person who plays them, they haven't got a leg to stand on. Supreme Court > ASCAP.
If the record companies had their way, they'd make it so that every person listening to a song had to pay a fee each time they listened to it; they look at the PPV business model and start drooling. They most certainly do have a problem with "borrowing a buddy's CD and copying it," and it's really only a matter of time before loaning your friend a CD or DVD just to listen to/watch it becomes legally questionable.
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