There are a lot of straight white dudes who are absolutely losing their minds over these two individuals. A number of us straight white folks are having a problem understanding why Dolezal has been vilified while Jenner has been lauded. I am here to talk to my fellow white folks who "just don't understand."
Race is different from gender. I know you know this, but we're starting at the beginning. One of the biggest problems right now, post civil rights act, post MLK.. but decidedly NOT post-racial is that white folks think they can multiply the worst interaction they've ever had with law enforcement by that time they were poor in college, add that unpleasantness with the bank manager that one time and divide by the number of hip hop albums they own and come up with a mathematical formula for the life experiences of folks of color. It simply doesn't work that way. This deafness to what people of color say, and the bone-headed ignorance of the very simple fact that if it were that goddamn simple people of color would have done that by now. Is the festering heart of institutional racism. So for a white woman to engage in a decade of lying and subterfuge to pretend to be black. To make her living off of the struggle of African American and Latino folks, to tell a Latina student "you don't look Hispanic enough" is precisely this deafness, this denial of black and brown people's own agency. You simply don't get to come in and "identify as black." There is a culture and an experience that you have never had that is precisely what it means to be a racial minority in America. To think you know what that is and what it means is the epitome of racism.
Jenner is completely different. She has never tried to explain what it means to be a woman. Before he transitioned, everything was completely out in the open. There was absolutely no subterfuge. No pretense that Caitlyn was never Bruce. If Dolezal had been that open, if she had been a white ally instead of pretending to be black, if she'd have listened to those who had that experience and then spoke from her own experience.. there'd have been no problem.
In short Caitlyn Jenner is trying to be who she is, Rachael Dolezal is trying to be someone else and that is the difference.