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I love the idea of a great-granddaughter being name after her great-grandfather. That gets 20 million bonus points! Without the backstory, I think Ottoline is pretty silly, but with the meaning and as a middle name it totally rocks. I might go with the -een or -in pronunciation so it doesn't sound like "outta line". Ottilie would be adorable as well.

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Both combos are okay. I feel like the both have a number of sounds echoed between the two names. But that's not a bad thing, either.