I've never really felt all that restricted by the DRM. Occasionally I'll want to send someone something and can't, but it's pretty rare, the majority of the time I just enjoy the music that I bought and don't even consider it.
I think Music piracy is incredibly lame and I wish that people did not do it, and though DRM is not perfect, I think that iTunes couldn't have gotten off the ground any other way. Now that DRM is going the wayside, I hope that users remember that music is worth something, and just because they can share it freely now(again) doesn't mean they should do it unfairly.
However, don't the DRM-free files still contain your account information in the id3 tags? so you can't necessarily get away with massively distributing or pirating the music despite being capable of doing so.
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