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You cannot de-DRM books delivered directly to the PW and the Oasis, AFAIK. You can de-DRM them by using the Download and Transfer with USB option.
Calibre collection management won't work with newer Kindles. Sideloading works as before, but it's better to use azw3 instead of mobi.
Why consider Kobo: they integrate better with Calibre, including series and collection management. They have more customization options and you can patch them to add even more (relatively simple even for someone knowing nothing about coding or programming). Kobo Libra H2O is cheaper than the Oasis, but nearly as good (or even better, depending on your viewpoint). Also, Kobo readers will get the excellent Oxford dictionaries this October (Kindles use Oxford dictionaries; Kobo dictionaries were considered pretty poor in comparison).
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