Caitlyn is a wealthy white woman who spent a majority of her life outwardly as a wealthy white male. The reality of female oppression is something she never had, and never will, have to deal with (excluding transphobic comments) For her to say the hardest part of being a woman is choosing what to wear is fine from her. She's newly transitioned and, like many trans folks, her appearance is extremely important to her, especially in the beginning when they're trying to develope their style. She's also a celebrity who's every move is criticized. She's facing a reality very few people will ever experience. Does she need to be educated? Yes. There's also plenty of cis women who are just as ignorant, if not more so, to issues women face; but, as a newly transitioned woman and her place in society, she shouldn't be deemed the face of feminism or trans awareness. She's still learning what it means to be a woman and unlearning the privileges she gained while living as a man.
Let's not forget that these awards, like all other, are of kind of bullshit. People keep responding that Cailyn is undeserving because "Kids are fighting cancer! There's female soldiers!" yet they don't seemed to mind the "undeserving" cis women who have received the award before. Rebel Wilson, Rita Ora and Jessie J are all past winners. Was there this much of a backlash against their wins? Nope. Have either of them done anything to change the world? Nope. Two of them are, at best, the most mediocre singers in pop, the other is only famous for being the 'funny fat girl' in a few extremely shitty movies. Caitlyn also wasn't deemed "Woman Of The Year" she was one of the 25 women given the title. The idea that a trans woman is the woman of the year vs a woman of the year seems to piss everyone off. The "real women deserve it more" comments are absolute rubbish and is the exact reasoning behind Caitlyn being chosen for the award. She's coming out in a time where trans acceptance still isn't where it needs to be, hell, people in the lgb community aren't even accepting of trans people, much less the general public. For her to have been in her 60s and making the decision to live her authentic life is extremely brave on her end. We're so easy to give every gay and lesbian that comes out so much love, respect and awards, but are still 20 years behind on trans acceptance, equality and visibility.
Also, let's not forget when Rose extremely generalized the gay community and called them out for being not being feminist despite the fact that some feminist tended to be very exclusive, herself included. Inclusive feminism has, for whatever reason, just taken off even in the past few years - though it should've been the core idea from the start. She should probably educate herself on the exclusion gay and trans folks experienced from feminist. Though, many great feminist have fought for the rights of the lgbt community for decades, there's still transphobia amongst some feminist, which is extremely ignorant. I'm a feminist, but I'm willing to call out their transphobic bullshit, Rose's included