* Status Update by Alice Marwick - an ethnography of the SF tech scene in the mid-late 2000s, a very detailed examination of the status structures in Silicon Valley and how we were changed by the rise of social media.
* Postscript on the Societies of Control by Deleuze - short, insightful, somewhat prescient paper on the evolution of "control" mechanisms in postindustrial, capitalist societies.
* Capitalist Realism: Is There No Alternative? by Mark Fisher - a very compelling analysis of the neoliberal postmodern condition, and how the cultural milieu has changed since the fall of the Soviet Union, and free-market capitalism became the only extant economic system in the world.
* Death and Life of Great American Cities by Jane Jacobs - this probably needs no introduction; it was an extremely transformative treatise on urban form, vitality, diversity, and completely overturned the urban planning field when it was originally published. I think everyone who plans on living in a city should read this book.
* Hollow City by Rebecca Solnit - an ethnography of the gentrification and bohemian displacement in San Francisco during the dot-com boom of the 1990s. She doesn't just blame "the techies" for the gentrification, but rather uses the gentrification as a lens to examine the culture around urbanism has changed in the recent decades.