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1. My favorite spelling is Schuyler, probably because it's the most legit, followed by Skylar. Also, I prefer this name for a boy.
2. I guess Skylar looks the girliest and Schuyler looks the most masculine, but none of them look particularly feminine to me.
3. Schuyler would probably have some issues with pronunciation, yes.
4. Any of them would be fine for the nn Sky.
5. I don't know any.
6. I don't think it will become more common.