I think this kind of thing is even worse for video games and applications.
If you go the legal route, you buy the piece of software, and depending on how they worked on their anti-piracy scheme, there are rootkits, spyware, malware, CD-keys (that can go missing), original CD checks. On more expensive software, you sometimes have to actually call the company and verify with them face to face. With all this, there is a high probability of verification servers being down, CD keys being wrong, bugs, errors, phone operator availability etc.
Obviously none of this has stopped the pirating community. If you go this route, you just download the game, install it, copy the crack over, and play/use.
I don't think I would ever legally download music if I even liked any of it (I'm not a music fan much). It'd be too big of a hassle to keep track of how many mp3 players you've actually copied the track to. Also hard drive crashes would completely ruin your collection. Ugh.
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