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Hi Scott, the first thing that I thought of was that black hair would make everything more obvious. It would bring more attention to the top of your head and anything going on up there would be more apparent. Definitely go to a salon and see what they think, they get this sort of thing all the time so they have ways to minimize it.
I dyed my hair black a few years ago on a whim and it looked ok a few weeks later but at first it looked artificial, the color was too black and it stood out more than usual, so I'm thinking dying it black might bring attention to it.
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