Sorry Buckhorn, your post was so text heavy it was hard to read. I do realize there was a time for things such as a Black Miss America, but I feel that time has passed. It is fairly routine for a black woman to win. One day I pray I will see a time when their doesn't have to be the celebratory message, "Only the 3rd black American to..." If I were black I would find these "qualifiers" offensive.
As far as all the stuff you typed about looks, fitting in, etc., you can't hang that on white people. That is on,if we are talking about blacks, black people. I don't see Asians, Vietnamese, Indians, Hispanics or other races lightening skin, dying hair, changing eye shape etc, to "look white" and they seem to be doing just fine in America, in fact prospering.
At some point, you got to lay down the load and own what is happening (changing looks, having poor self esteem I guess?)
And by the way, I have wavy curly hair and straightened it for years in high school, and the did say eff it and got a haircut that works with the waves.