Kindle Collection Manager?
I have over 100 ebooks, and it's very tedious to add them to collections one by one on my kindle. Is there a way to add multiple books to a collection while my kindle is connected to my desktop? Calibre? Or is this program, Kindle Collection Manager, a way to do that? Has anyone tried it before? What was your results?
If I were you, I would let Return of the Jedi serve as your model. If you remember, there were a lot of eBoks in that movie, and they all lived on their own planet. Left to their own devices, the eBoks organized themselves into a lively and fun-filled society that was capable of defending itself in a pinch.
This is probably a lot better than mixing them up with things that might start fires.
I'd go with Calibre, as it is Kindle compatible and multi-device friendly. This means that as long as you have a clear idea of what you are doing, you'll only need to do it once, and yes, you can drag and drop multifiles at once using it.