The "extra" application is really very simple and does not take a rocket scientist to figure out. All you do is drag and drop onto the reader and you're done. There are also alot more choices to buy drm-ed content for the sony, and sometimes they even end up cheaper than the kindle. The price of kindle ebooks was totally irrelevent to me because I knew I'd be getting a ton from the library to offset that. The 505 is around $100 cheaper and comes with a case, so that extra money can be spent on ebooks. I really did consider the kindle and was actually getting ready to buy it, then I rethought my decision and went with the 505. I am by no means tech-saavy (I don't know how to convert, format shift, etc). and the Sony is just fine for me.
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