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I don't have to go through that many steps to sideload to my GL4e either, but it's definitely a little strange. I just use the "Send to device" function in Calibre, but then it seems like I usually need to reboot my Nook in order for the books to actually show up. And then occasionally, they just don't seem to make it so I have to try to send them again. But most often, it really is just a matter of sending from Calibre and then rebooting.
I use KOReader on my Nook now, but I'm pretty sure I had some similar weirdness with sideloading when I just used the stock app too.
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