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The only suggestion of David that I would use would be to use the cloud connection to automatically download all new books into CC once a day. I haven't suggested it, because it seemed like a lot of work for a little benefit. As a middle ground, perhaps once a cloud connection has been established, maybe have an option to download everything new.
That middle ground already exists, with the Reading List plugin. You tell it to make a list consisting of all books, and that new books on the list should go to the device. Whenever CC connects, all my books download.
That is not the problem.
The problem is getting the connection to happen. I really don't want to run Calibre all the time (Although I've pretty much decided I have to), and the wifi on my device (A Boox Afterglow 2) is a bit wonky (CC can't turn it on, although I don't know if it even tries to do that with a scheduled connection anyway.) and often disconnects when I have no data transfer, despite the fact I told it not to do that.
At this point I have CC on a timer for each evening, I deliberately leave my computer on, and Tasker flips the wifi off ten minutes before the CC scheduled time and then on one minute before it. It...seems to mostly work. If I remember to leave things on, and I'm actually at home. (If I am not at home, I have my ereader with me!)
The reason I am unsatisfied is that...I have a half a dozen things that sync offline, on both my ereader and my Android phone, and *every single one* of them is completely automatic and less work than dealing with CC. All of them just stay synced, period, thanks to timers turning my wifi on and off so they can do that.
And my books *also* used to work this way, where they all got exported, via Folder Device, to a folder in Dropbox that magically, with no effort on my part, got to my Nook STR.
Worst case scenario is that I whisk my reader and phone out of my house before things sync, at which point I either have to find wifi or use some data/tether it to my phone...neither of which I can do with CC.
And, hey, CC supports a cloud connection, right? We can use that to sync, or, better yet, just sync the entire dir offline, so I set that up...oh, now I have to track down stuff that isn't on the device and add it. Also, I've now got two entire copies of the library taking up space on my device, nice. Well, this *almost* works.
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