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It is not clear to me what the point is of inserting old Clippings into new Clippings. This is just a log file, it does not contain the actual book annotations. There are better ways to back it up. And if Clippings gets too large, it can slow things down.
I would think clippings.io is smart enough to merge new annotations with existing ones in your Evernote notebook (e.g. same as if you were reading the same book on more than one Kindle).
Also if you are not aware of it, you can Export notes from Personal Documents with the Kindle app on Fire, iOS, or Android. It can go as an email attachment (e.g. email it to your Evernote account). And you can copy/paste to the Evernote app.
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