If you're coming to the table with many sideloaded books, pass on the Kobo. The Kobo excels with their own books that use a rendering engine different from Adobe's. With these books you'll be able to take advantage of all the features of the Kobo. Many of those features are not available with regular Adobe DRM books or even books that have DRM removed. You can get specifics by posting in the Kobo forum.
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