I agree, it's a weird argument! However, if the points you paraphrased are supposed to be the premises, I'm not sure why they're inherently false. Maybe I don't provide ample research behind them. But are they obviously false?
1. Did an explosion of literacy due to the printing press lead to an interest in free speech? Makes sense.
2. Does endless debate / political gridlock lead to an inability to build in San Francisco? Every attempt to provide housing becomes a vicious argument between NIMBYs and YIMBYs. I also have personal experience working both sides of local development issues in Austin, and the challenges are similar to the ones in SF. As you're trying to go about your business in city council, someone will stop the conversation with some objection to an act or policy that would make everybody's lives better except for that one person (so they think), and then nothing gets done, or it requires expensive lobbyists to push through.
3. I don't have an objective backing of my city ranking, but I've socialized this high-density / high-functioning metric for some time now, and anybody who has traveled has agreed with my assessment with Asian cities. Note, two cities I mentioned are not in China: Tokyo and Singapore. I also forgot to mention Taipei, but that belongs on the list too.
4. I don't think free speech will doom the West. And that is not a premise anyways.
However, if there is a takeaway, my hope is that the West takes a deep look at itself as to what works and what doesn't work with its culture, and try to evolve without losing its soul. Barring that, then accept that as Asian cities evolve and support greater populations, the U.S. will be relegated to a minor player role, similar to the U.K. today. I just hope I don't grow old and discover that my beloved America is having its own petulant version of Brexit.
1. Free speech leads to obsession with texts.
2. Textualism is responsible for ills like the San Francisco housing crisis.
3. As the author has personally ranked favorite cities, the best ones are in China.
4. Therefore free speech will doom Western society.
On the bright side, if an argument isn't valid, it doesn't matter as much that your premises are false.