Nice idea! Your request reminded me of two similar pieces, which I'm pointing you to for inspriation.
First, you might like this guy's take on everyday architecture and life in SF. His (usually single panel) illustrations ran for a number of years in the local paper:
Paul Madonna - All Over Coffee
Second, here is a collection of prints that were created for the national park that covers most of our coastline:
Regarding your project, the next few I'd do are Muir Woods, the Pier 39 sea lions, the Ferry Building, and AT&T Park.