Making the Kindle Paperwhite 2 Useful for an Avid Reader...

... With an outrageously large digital library.

As I was trying to set up my Kindle to work with Calibre, I realized that over the last six years or so, I have gone through A LOT of ebooks, and I have them downloaded from all over the place -- Baen, Tor, Project Gutenburg, Smashwords, and all of the major eBook retailers. The smallest part of my library is Amazon (only 169 books). That's why I was desperately trying to get my hands on a Kobo Aura (but not so desperate as to order direct from Japan on ebay). Almost 4000 books, novellas and short stories in epub or PDF format (not all of them read, mind you).

So, this past weekend, I went through database hell. I started working on the +How-To Geek  Screensaver Jailbreak --which really needs to be updated to state 1) it doesn't work on the PW2 and 2) if you attempt it anyway, DO NOT register your device and get the updated software because then you are SOL up a river without a raft, with a flash flood headed your way--so I could install the Collections jailbreak and at some point my brain went EFF THIS! Way too much work and I am not too thrilled at the possibility of bricking the thing. I had already started organizing things on my Kindle app, because cloud synchronization is a good thing, right? RIGHT? Yeah, right.

By the way +Jeff Bezos , find some competent programmers PLEASE. The Kindle for PC app sucks sweaty monkey balls and won't import collections from my Android (Nexus 7) nor from my Paperwhite once I connected it to the PC. Nor after creating some non-duplicate collections would it sync to the almighty Amazon cloud so I could sync to my Paperwhite. So now I have Collections in three places that don't sync.

When I synced just 4 collections to test the functionality, I was pleased. When I went back later to get the rest from the Amazon Cloud, they wouldn't download. (At this point I learned how to take a screenshot on the PW2, but since Collections are part of a smart menu, it didn't take). Oh, and update the Kindle help articles to reflect what actually happens and what the PW2 is (not) capable of.
Solved: From the home screen I hit "Search" and searched for my missing Collections and from there I was able to download my collections from my Nexus 7 to my Paperwhite. Not intuitive in the least!

I kept looking for a solution to getting Collections synced without jailbreaking. One article stated that you could organize your collections from the Kindle Cloud (maybe they meant this help article?), but that functionality does not appear available on the Chrome app (seriously, WTF!?! How many serious readers do you know who just toss their books anywhere and don't have some sort of organizational system???) So for now I am stuck creating collections on my Nexus and importing them to my Paperwhite. It's just plain faster on the tablet, but would be even better if I could do it from my computer. And oh yeah, then there's the issue of downloading the collection and then individually importing those books. Who designed this setup???? Everything says that I should be able to manage collections from Archived Content, but that section isn't on my account.

Another gripe that has made getting a Kindle tortuous:
Kindle has changed their interface so much. I went into Manage My Kindle (now Manage Your Content and Devices) and you can delete items, but you can't archive them. In fact, there is no archive (well, that page is the archive but there is no differentiation between active books on your devices and "archived content", you know, like your Nook Library) and no way to manage your Collections on the web. I just want to be able to organize my books -- quickly and efficiently en masse. Why is that so hard for Amazon/Kindle developers to understand?

Poor Calibre is still importing and updating metadata. I had my ebooks in three different cloud areas, and that does not include Nook, Kobo and Kindle books stored online. I haven't even finished downloading my Nook Library -- while I had it, I used Free Fridays every week, often getting up to 10 books each week. It doesn't seem like hoarding when it's digital. Until you have to organize it.

While I was writing this, Calibre crashed and burned. I had to start over. Doing small batches of only a few hundred books at a time, just getting the metadata at this point and then I will sort into series and virtual libraries.

Conclusion: After nearly 48 hours of wasting time researching and trying out solutions from 2012 -2014 that say they are for the Paperwhite, you really can't make the Kindle Paperwhite 2 useful; not even for Amazon bought books, let alone books in other formats. I will have to keep the Kindle app on my tablet so that I can tediously organize, and then head over the PW, search and download the collection and then each book individually. 

If you have the Kindle Paperwhite 2 (software version 5.6) and have figured out how to do this, will you help a sistah out?