I have a question. It’s one I’ve been wrestling with for a while now, and don’t have a definitive answer, as you can make arguments for both sides. It’s not the one in the title, we’ll get to that in a minute. The question is this:

If you own a vinyl or cassette version of an album from a record label, does that entitle you to the digital representation of that album, even if it was ripped from a digital source that you didn’t pay for?

The easy answer is “no”, and I would say the argument for that goes something like this (the need to make more money aside): if you only had to pay once for a recording, going from vinyl to cassette to CD would be a simple trade-in, maybe with some compensation for the media itself (which is more substantial with new media formats, but over time goes down dramatically).
The not-so-easy answer, “yes”, opens up more questions. Let’s assume that I’m honest, and all I want to do is to enjoy the music I’ve already purchased on some form of digital playback device (computer, iPod, whatever); I’m not planning on sharing it. Fair use says I can make a backup copy of the media I’ve purchased. Then the solution becomes: well, just rip the original media. Let’s say, however, that I no longer have access to the necessary equipment to do that (which is true: I no longer have a record player). Do I need to invest in obsolete equiment (sorry, DJs/audiophiles!), not to mention the pre-amp I’d need to get the signal into the computer, to get music on my computer, when I can just grab it online somewhere?

I’m not a lawyer, and I haven’t researched this question, so maybe legally it’s a cut-and-dried issue and the answer is “no”. But that then leads to the question in the title: What are you paying for when you buy music? If the answer to the first question is “yes”, then the answer to the second question is easy: the right to listen to that music in any form, anywhere. If, however, the answer to the first question is “no”, then the answer to the second question is along the lines of “the right to borrow the work to listen to it as long as you’ve got the technology to do so in the purchased form”.

Which means it’s not about the music at all, it’s about licensing the right to something. Now I’m not so naive that I think it’s not about licensing, and I’m all for artists being compensated for their work, but when I hear how dismal that compensation can be sometimes, I can’t help wonder who I’m giving money to when I buy a CD of an album I already have the vinyl or cassette of, and why I need to be doing this when the music I thought I had already purchased is a few (questionable) clicks away.

Oh, and before it’s pointed out that $0.99 per song on iTunes isn’t that much to get the digital version of a song, I will agree with you as soon as iTunes gets a comprehensive collection: for the current size of it, I still can’t find most of my older music on it (and I’m not even going to touch the DRM issue).

I could get into analog vs digital copying, and other side issues, but I’m not sure that’s relevant. I just want to know if I really need to pay to have the ability to enjoy all the music I’ve spent money on.
What do you think? Does anyone know the definitive legal answer to this? Have I missed anything obvious?