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I wonder what would happen if someone was sued for having only DRM-stripped titles (which can, somehow, through metadata for example be proven to be content that is sold only DRM-protected) on their Kindle, and then the person provides proof that these are all books she has bought from other shops e.g. as epubs and then stripped DRM and converted for personal purposes in order to read on one's preferred reader.
It's still a violation of something, yes, but would any court actually find the person guilty of something and punish the person? That would be an interesting case, really.
As for the question of what happens when sideloading stuff ... as far as I can tell, books I've sideloaded to my Kindle via the USB cord, with the Kindle's wifi switched off, only appear on the Kindle, not in my Amazon cloud. If I've either emailed the books to my Kindle or used the Send to Kindle PC application (the latter allows me to specify whether I'll want to save it in the cloud or not), the books will show up in my Personal Documents list under Manage my Kindle and I can also download them from the cloud/archives on for example my phone or iPad, in the Kindle app there. I'd be highly surprised if Amazon didn't have access to the metadata of those "personal documents".
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