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Cannot comment on jailbreaking (my Kindles are not jailbroken), but sideloading is by no means crippled. All my books are sideloaded via Calibre. Most of the features are available for sideloaded books. It's true you have to sort the books into collections manually on an un-jailbroken Kindle, collection managers work only with jailbroken Kindles.
Personally, I have never felt the need for jailbreaking. Sideloading and all the other things important for me work just fine without it.
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