As someone who lived in West LA for years and saw the new line come in, I'll stop you right there. Cities like LA, Mexico-City, San Jose, etc. are not well designed and trying to re-invent them is going to take one hell of an earthquake.
I used to live at 16th and Santa Monica and was really excited about the Expo Line. I ended up moving before it showed up because it was many years late (I'm glad it finally got built though!)
I used to ride a recumbent to UCLA now and then because I had a death wish, and it shocked me that it took 25 minutes and yet people spent 60 minutes in traffic in their cars every day just to get across the 405.
You're right, though, those cities are mostly lost causes, more for the attitudes present in them than the infrastructure. Doesn't mean we can't try to make any new ones better though.
Oh man, the Expo line isn't synced with the lights, it's horrible. That and the bums like to go crazy and sit on the rail lines, causing jams at the street crossings. It's not that frequent, but it happens. It used to back up to Bundy on a bad day, now it's every day.
Riding a recumbent to UCLA from 16th is hardcore. Everyone I knew that rode in west LA got hit at least once, if not more.
Just ease the regulations on building height and density, and multi-story multi-family buildings will start to appear in good locations through free market capitalism.
My brother lived off Geary for a few years and went to a few public meetings on the proposed subway line they want to put under it. He was interested in the idea, as the N-Judah is a methadone clinic (last he was there a few years ago, caveats apply). He never saw such NIMYism and such tight resistance by the property owners on Geary to any improvements whatsoever.
You don't just ease regulations or really do anything 'big' in any city. Palms must be greased, and if you do not it is a horrific process that takes at least a decade.
I'm not saying that you are wrong about the free market. However, my brother thought that the most fantastic thing about the new Star Trek movies (esp. the new Wrath of Khan) was not the warp-drive, nor the aliens, but the very tall building in SF. Even in 400 years, there is no way the planning boards would allow such things.
The San Francisco Board is subordinate to the laws of the state of California. If California wants to ease regulations against denser urban areas, California can do it.
I mean, you aren't wrong, but you are unrealistic. Something like that will take years just to get to a final vote, and then the lawsuits will tie up the issues for at least 20 years. Say 30 years total, just to get to the point of a permit to build. To get things moving faster, you may need to re-write the CA constitution.
As someone who lived in West LA for years and saw the new line come in, I'll stop you right there. Cities like LA, Mexico-City, San Jose, etc. are not well designed and trying to re-invent them is going to take one hell of an earthquake.