Thanks to all who replied, I really didn't understand what CC is (still don't actually) and thought it was a form of Calibre for iOS. I gather that there really isn't an iOS version of Calibre. I have never used the Kindle browser, so I don't know how it "sees" the library if I upload it to Dropbox. Don't have or use Amazon Cloud. Yes, it is a Kindle Paperwhite and not a Fire.
Although I am a bit confused by some of the replies, it sounds like the iPad won't play a role at all in facilitating transfer of the files from an HD to the Kindle and the process will have to rely on the Kindle Browser to transfer then?
I will have to research what a Calibre server is and how it functions and how it is different than having the Library on Dropbox. Odd that there is no easy and elegant way to put books on a Kindle from a Calibre Library without using a computer with Calibre installed. However since I've always done it that way myself, I could be missing a way to do that I'm not familiar with.
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