I empathize with most of what he writes, but an irritatingly common pattern I notice when people criticize SV is pointing at destitute people next to wealthy people - as if proximity is the same as causality. California has more than its share of destitution, but fifty years of NIMBYs and catastrophically bad housing policy are a better candidate for blame. If you make housing expensive you shouldn't be surprised when people go unhoused and when everything becomes expensive because labor (which has to be housed) is expensive.
To be fair it does seem pretty random when stuff gets taken up and when it doesn't. AFAICT sometimes content that ends up very popular is ignored the first few submissions.
For people who point out that this incentivizes companies to leave San Francisco, that's probably not a coincidence. Many SF politicians see tech as the enemy and would be happy to see companies go elsewhere.
I briefly tested it with 'That doesn't make sense.' which worked, but switched back to yo because I'm looking at the probability of the first word and 'That' is too common to assume that the rest of the completion is 'doesn't make sense.'