One point is that his take on the "technological vastness of the future" we now live in has become so circumscribed that his advice WRT to is is getting less and less relevant.
At another level it's making him more and more ignorant, since the price for him to do the research necessary to chart wise paths in things like FSF/GNU governance is so high.
To draw back from the weeds, how can he be "The Hero the Internet Needs" when he is so disconnected from it? Per the essay, his argument has no nuance, it is to not be a part of this thing which, at least to my paranoid mindset, is indeed just as dangerous as portrayed, but which offers vast benefits for being (a careful) part of. Especially for the vast majority of us who, aren't, you know, (any more) a part of the MIT community or the like.
ADDED: Maybe to draw back even further, he's not wise; that doesn't disqualify him from being A Hero of the Internet, but it's a significant thing.