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Thanks for all the comments - you've jogged my memory further, the problem I ran up against before wasn't sideloading, it was organising sideloaded books into categories. On the older kindles there was a plugin that could arrange books into categories based on a column/tag from calibre. With the newer kindles, it seems as though that plugin doesn't work, and so the only way to organise is by jailbreaking.
But as long as that's the only limitation, and I'm happy jailbreaking to get that functionality, it looks like I'll be getting a PW!
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