A lot of his points are cogent and valid.
It’s wrong to say that in previous generations Shidduchim happened organically, without a shadchan, with people asking each other out. That’s untrue. Perhaps in certain American communities that was done a generation ago, but that was never the way it was done in the Torah world. Yiddin used Shadchanim.
I don’t have solutions.
I don’t think that recreating our norms regarding Tzniyus and interactions between boys and girl is the right solution. I think that people who know what the Torah says (which is the primary definition of Daas Torah) all agree on that.
His argument that failure shouldn’t be rewarded is compelling. But I don’t think free market capitalism will solve the problem.
The other two jobs where you can be wrong and ineffective most of the time and keep your job are being a weatherman and a politician. In both of those fields I dint see any improvement.
The wish I had a solution.
I don’t think he does, either.