For sideloaded books, connect the device and start calibre. Then, select the sideloaded books, right-click and select the menu item to add the books to the library. That should add all the DRM sideloaded books to the device. From memory, you can select all the books and it will add those it can, and display an error for the rest.
For books from Kobo, you should be able to use the Obok plugin that is part of the DRM Tools package. That can handle books with and without DRM. Or, use the Kobo desktop application to download the books to the PC and then use Obok. Or download the epub version from you library on the Kobo site.
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