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Steve, why use the example of downloading from iTunes, a commercial entity? Try any P2P network. They host a server, while not strictly legal in itself, that provides me a MP3 for a CD I own. Guess what? I'm clean-and-legal. Goes back to how bits have no memory. It does not matter that some scum-of-the-Earth posted it. If I have legal use of it then the transaction is clean and even ethical on my end.
No, iTunes will not provide me that free converted file. Though I could argue that since their software includes a ripping package that they DO in fact provide me that service for free.
On a side note, I once needed a book that was out of print and not available. It was factory repair manual for a rare motorcycle. Before purchasing a xerox copy from a fellow owner I contacted the manufacturer, still in existence, and got their permission. That is one way to deal with the out-of-print question. I expect most copyright holders would permit e-version access, assuming they had zero expectation to bring the publication back to market.
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