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I came from a K4NT to a PW3 and had the same issues with collections, I knew there was no jailbreak and id not be able to do it via calibre but it was still a pain.
First and foremost id suggest a few things.
1) Use the Android/iOS Kindle app to create and manage collections, its much simpler and quicker.
2) Organise your books in Calibre convert to dual mobi and use amazons send to kindle feature which stores them in the cloud. This way you can assign books to a collection from amazons cloud via the android/ios app and they are forever in that collection until you remove them so if you need to wipe or get a new kindle the books are still organised you just need to re-add the collection to your kindle.
3) Be patient, there IS a jailbreak for current firmware PW3 it just hasnt been released yet. It was supposed to be released last month but amazon asked the guy who found it to wait so they could patch it. Stick your kindle into airplane mode on firmware 5.6.5 and wait it out.
Ive done all the above so could happily live with my kindle un jailbroken but will wait and see if the jailbreak gets released and use that.
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