I just left SF after 20 years. I had enough. I now live in Manhattan — where rent is CHEAPER than SF.
One thing you left out about SF’s (in)ability to grow-up into a Prague or Milan or any other semi-functional high-density city:
Lack of a functional (i.e. reliable and meets demand) transit system.
It would take me 45 minutes to DRIVE off-peak to my office in MtView — to take Muni+Caltrain it would take me — best case — 2.25 HOURS.
Without reliable a transit infrastructure SF will NEVER become a functional NYC, London, Paris, Tokyo, et al because it can’t move people around efficiently.
I actually think this is intentional as not only are housing and transit constrained so is water and power — also cheaper in Manhattan.
Unless there is a serious plan to make long-term infrastructure investments, SF will remain the world’s largest small town.