I have tried both Kindle and Kobo, and like Kobo a lot more to read on. I think Kobos usually offer more features for the price - better screen, different screen sizes, more organization features. It's easier to find the book I'm looking for. Kobo has a store and you can find all the usual books on it, so you can buy books just like normal.
Transferring existing books via Calibre is very easy: Download and install Calibre, install the right Calibre plugin from Apprentice Alf, import all your books and then convert them to epub.
That said, if you just want something that's super simple, get a Kindle. The important thing is that it work the way you want it. There's nothing wrong with Kindles, or with wanting something that just works the way you expect it! My friends who like their tech to just work have Kindles and are very happy with them.
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