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I think Winona is a fine choice. It's feminine and has the long "o" my ear fancies. It can feel sweet and wild or seriously intellectual. Sure, folks may be reminded of the actress or country singer and may or may not consider those individuals to be positive associations but I can't see how this should be a real problem. There are names I won't personally use due to negative associations, but these are real biggies like Adolf and Lucifer (I really want to consider the latter usuable but just can't). Our celebrity Winona's, while fallible humans like the rest of us, certainly aren't in that category. :)