Dragonbone, I can't speak about the Sony software, because I never installed it, but if you use Caliber, it's pretty easy to put things on the device. Just highlight a book in your library and click "send to device". The hardest part with Caliber is procuring the books, since it's not integrated into any kind of store. You'll have to download them on your own and then "add file" them into Caliber.
Alternatively, when you plug in the reader, it also shows up like a USB thumb drive, and you can copy files to it. Or you can copy files to a memory card, and then put the memory card into it.
It's probably not quite "Kindle"-easy, but as far as tech stuff goes, it's definitely way up there on the "easy" scale.
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