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I have the PW2 and while the free tools and jailbreaking are useful and very helpful, I am also one of those ones who do not jailbreak because to keep up with them requires a lot of hoop jumping to stay abreast of all the updates. This is not a moral decision for me, just a "I am too lazy to keep up with it".
With that said, I manage my collections strictly through Amazon's tedious collections and Calibre's plugboards. I currently have over 5000 books in my collection which includes all my purchased books, free books as well as Overdrive borrowed books. I have over 130 collections which I use to manage them. And let me say initially managing them was a tedious job, especially when Amazon introduced Cloud Collections. When you first start out it is quite a lot of work and patience to set them up but maintaining them is hard. Calibre and it's plugboards helped me to get everything where it needed to be, and it helps to keep them maintained. I strictly use Calibre to put books on my device.
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