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TBH I might be inclined to put up with the DRM if the Kindle reader was also usable for other things (PDFs, ebooks purchased from other vendors)

But the library management is broken/non existent

So it's not just that you can't read Kindle books on other devices, but the Kindle itself is pretty much useless for reading things you purchased from other stores

Even though it was cheap and 2nd hand, I regret buying this thing

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Jailbreak it and install KOReader[0], which supports PDFs. You can also install something like Project Title[1] for a fancier UI

https://koreader.rocks/

https://github.com/joshuacant/ProjectTitle

Have things changed recently? Sideloading books has always been well supported in every kindle I’ve owned, though admittedly my current model is 3 or 4 years old.

Sideloading is still supported. But Amazon removed the ability to download your legally purchased (rented) from the Amazon website - the download and transfer via USB option [0]. So if you previously downloaded those books, you can still manually copy them onto the Kindle.

[0]: https://goodereader.com/blog/kindle/amazon-removing-download...

It was possible to load other files on there and read them, but there didn't seem to be any way to organise them. The UI and tools seemed really crap.

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