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You can use collection just on the kindle not that easy at first you have to connect to the cloud but once you have connected and setup on device collections you can go to air port mode and side load your ebooks, I do all the time using calibre. I have never had kobo so I do not know it, I have had one of the first ebook readers that was not tied to any of the ebook systems. And I liked it. I am on my second e-ink kindle, and I have also had the very first kindle fire. I love my PW2, an I am not even thinking about the newer PW3 I see nothing about it that I really need. The screen on the PW2 is great for my reading and I do not use any note taking and only sometimes check works in the dict.
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