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I have paid one or two dollars on the Kindle store for books I could have downloaded for free because when you buy a book from Amazon, they keep an archive of it on their servers, including reading position, bookmarks, and annotations, and they synchronize this information across all of your registered devices. The convenience of this feature, along with better formatting, has sometimes been worth the money.

I have done the process of downloading and copying to the Kindle for some works that were either not available in the store. Although it's not difficult, it's not as easy as the Kindle store. This is another case of sometimes easy beats free.