Stezza puts forth an excellent argument that I feel hit the nail right on the head. I do not re-read books so there is no sense in me re-purchasing the ones I already have.
I dont think that piracy has anything to do with anything when it comes to ebooks. Lets face it... you can find books out there. The formatting may be a jacked but you can still read them...
It has been mentioned before that anyone can sit there and listen to music... not everyone can sit there and read. Well, let me take that back. Anyone can do it, they just dont. It is much easier to sit there and watch TV, play video games, or listen to music... and I think that is one of the big challenges.
Not to mention that is irritates me to see that the price of an ebook is the same (or almos the same) as a paperback. What is the point or paying almost $400 for a device that is primarily used to read and does nothing else and then I am to pay for ebooks almost the same amount as my neighbor does for hers. (I know you can listen to MP3's but lets face it, an iPod is much easier, more portable, and cheaper)
Also... the new Kindle has store about 1500 book according to Amazon. So, at $10 per book (for new releases) it would cost you $15,000 to fill the kindle! I think they are banking on people either having a large collection of books or them getting them by "other" means. Hell, look at the iPod. 120 gigs!?!? That would cost a fortune to fill it with legit music/movies.
My $0.02

-Rob