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In my experience for your Bay Area use case, which is poorly maintained roads that will be littered with broken window glass and various other crap (hello construction screws), you have basically two choices:
1) Low pressure high volume tubeless (not narrow, high pressure, low volume road tubeless)
2) Gatorskins or Marathons
When I ran clinchers and commuted to and from SF every day, I constantly got flats until I switched to Gatorskins, which would still occasionally puncture due to the amazing amount of broken glass we have on the street.
When I started commuting on a gravel bike with low pressure, high volume tires... I never got a flat again.
The crossover point seems to be 35s. You really need to go up to 38/40s to get into the right pressure zone in my experience, but this will vary a lot based on your riding weight.
Of course tubeless is kind of a hassle for a commuter, but I am not sure if commuting is your use case.
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