I think there are a lot of interesting issues here.
It seems like the motivations for paying for a digital copy of the book are mostly along the lines of supporting the author. But as others have pointed out, authors don't get any support from used book sales, library loans, or books borrowed from a friend.
If you, as a reader, used to get your books from these sources, does downloading free ebooks now change the issue? and if you don't download free ebooks, what did this change about your book reading habits/budget?
And, in some cases, does the current status of the author matter? Does a dead author need support, or does J.K. Rowling?
Another motivation seems to be to support the idea of ebooks, and maintain a viable marketplace for ebooks. Does this extend to buying your favorites whether you want to read them again or not? Does it extend to buying the BBeB version of a Gutenberg classic?
It also seems that availability can affect people's choices. If you've bought a book that you can't buy the ebook version of, do you download it? Do you buy a second copy, perhaps, to make up for it?
If you do download ebooks of books you own, does it matter whether you bought the book new or used? What if a friend loans you the book and expects it back, but you prefer to read it on the Reader?
Is the relative 'polish' of commercial ebooks a factor in anyone's decision? People have claimed that iTunes' success lies, in part, in providing reliable, easy-to-find versions of songs. Pirate music, while cheaper, isn't as reliable or as easy to use.
It seems as though legality isn't really a huge factor on anyone's mind. I'm not sure, but I think this particular activity is in a bit of a legal grey area. Format-shifting hasn't been ruled to be either legal or illegal in a decision. (I'm not convinced an MP3 is a 'derivative work' of a CD, and I know no court has ruled that way...) Time-shifting is explicitly allowed, however (which doesn't hold much meaning for books).
I don't know if I added anything here. Just trying to summarize and probe what I think is a really interesting discussion.
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