As an SF resident I concur w/ most of what you're saying. For me it's not a deal breaker, but I can see how it could be. Almost every one of your bullet points can be explained by the phrase, "Liberalism gone nuclear."
[Expensive] -> Rent control and Private property restrictions. Housing supply is limited w/ endless permits and restrictions on building additions or subdividing space. And rent controls not only create artificial scarcity by not allowing price to rise w/ demand, but they also encourage people to stay in large places long after they need them. Imagine what the web would look like if you had to wait for months for a zoning board to approve your server expansion.
[Casual Food] -> Wait staff must be given minimum wage and health insurance whereas the wait staff in most other cities live off tips. What happens is restaurants become EXTREMELY expensive to run and they usually fire the wait staff at lower end places. You'll notice the order at register and take a number tag game played a lot to get around it. I know a few high end chefs who had to move their restaurants to Oakland b/c their waiters made more than them.
[Music] -> Don't have anything for you on this one.
[Cabs] -> Government set prices are too low. Demand exceeds supply at that price and there is an artificial shortage.
[Parking] -> Tickets are one of the most reliable ways to pay for all the hair-brained social experiments that take place here.
[Small] -> Fixed housing supply. See rent control / private property restrictions.
[Commute] -> I don't have an easy explanation.
[Filthy] -> Amen. We don't have a homeless problem we have a zombie problem. Your run of the mill drug addict is seen as a victim rather than a scourge. He is given food, money and shelter by the government to continue his habit. My friend worked for a non-profit in the Tenderloin that offered shelter, clothes, showers, haircuts and job help to anyone indefinitely as long as they submitted to drug tests. Their beds in 3 buildings were always empty and they shut down.
[Public Transpo] -> Make a bus driver too expensive by catering too much to the unions and busses have to get bigger. It's the opposite effect of the long tail. Instead of many small vans and more custom routes, you have few huge routes that serve nobody very well. Also the homeless ride the bus for free.
[Haight] -> In the late 60's the Grateful Dead and their followers began to get sketched out living there. Heroin and crime have been the norm there for years. It's foul and there is no police presence.
All of these policies had very good intentions. But the intention of a policy does not determine it's outcome. Furthermore, almost none of their side effects are ever measured by the government. It's fine if you want to experiment, but at least measure the result.