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I'm most likely naming my son Milo, partly to honor my father in law Myles. I thought about using Myles and calling him Milo, but then I think I would have to call him Mylo with a 'y' and it looks funny to me. So I'm kind of torn here too! I say use Miles and call him Milo. I have no connotations with this name, I don't even know who Miles Davis is! The only thing I can think of is the movie Milo and Otis (cute movie) which isn't a big deal. Every name reminds you of some thing, right? Good luck!