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I like Wynn a lot, so Win as a nickname I like too. I'm able to look past the word, and since it's a nickname I'd imagine he'd be called Win but not actually have it written down often at all. So the spelling wouldn't be much of an issue even. (Though I do appreciate your "Win being destined to lose." hehe) I think Edwin is very handsome. It's probably my favorite Ed- name. I'd love to see it use more and I think it has a smoother sound that would fit in today better than other Ed- names.