In general, I think Oberlin is way too complex for a single word (except maybe
this 
). What bothers me about "fearless", specifically, is that to me it implies recklessness or thoughtlessness, which is definitely not what Oberlin is about. While I understand that that's not what they're trying to evoke, it's hard to get across a more nuanced impression of the school when everything is branded with just "FEARLESS" in huge letters. (The new stories on the front page of the website are a step in the right direction.) The "we are Oberlin" also sounds weird - reminds me of
sports teams at huge universities or something. It's got a triumphant, monolithic, "with us or against us" kind of tone.
I also dislike the design of the "fearless" admissions materials. The bold neon scheme is kind of gaudy and generic, and they're too light on actual information about the school. They definitely didn't give me the impression that Oberlin was the peer of places like Reed, Swarthmore, Wesleyan, etc. Then again, my first contact with Oberlin was through the old admissions materials ("Think one person can change the world? So do we"), which were
very different...
Whew! That was cathartic.