When I first walked into Mark Donaldson and Dawn Judd’s loft in San Francisco’s Dogpatch neighborhood, their two daughters were swinging on climbing ropes hung from the rafters, and Mark was weaving between them on a skateboard. All the kinetic energy looked a bit dangerous, but also exhilarating. A pink bicycle perched on its kickstand near a door that led to the patio, and everywhere, about to topple, were stacks of books. The building once served as the Esprit headquarters, where Mark and Dawn both worked in the late ‘80s. Some 20 years later, while at a children’s birthday party across the street, they noticed the place was for sale. Now a bust of a girl with braided hair, sculpted by Dawn’s grandmother, sits in the entryway, and wooden birds float from the ceiling.

“ ‘Who is the rich man?’ asks the Talmud,” Sara Davidson writes in the opening of her 1979 essay “Real Property,” a homage to Los Angeles real estate. “The question has never seemed more relevant.” Arguably, the query is more relevant in San Francisco now. This city has long been rich, but rich in its own kooky terms: beauty, love of weirdos, dedication to the soft hedonism known as “the good life.” But now San Francisco is just plain rich — with money. Lots of it.

The houses we live in reflect who we are — our taste, what we value, how much we have. But the houses we envy? Those are purer expressions of ourselves, our desires unconstrained by little details like bank balances, allowing those homes to be three-dimensional renderings of what we’d like our near-term futures to be. I envy Mark and Dawn’s house, and in the envy chain that follows (the third the magazine has published), you can see which house they envy, and which house the owners of that house envy and so on. But the truth is: In San Francisco, this house envy is a socially charged game. The city is in the midst of an epic identity crisis — a battle for what it will become. Week by week the city is changing. Depending on who you are, the shift feels like the miraculous rustling of a golden-tipped dawn or the first rumblings of the Big One under our feet.

When I moved into my own humble home, the house across the street was occupied by three elderly sisters. The stairs were rotting, the peach paint was peeling, but the sisters stood on the porch in housedresses, chewing tobacco and warbling to the neighbors about the nice day. By last May, two of the sisters had died and the third couldn’t live alone. A development company bought and gutted their home, reselling it 10 months later for almost $900,000 more than it paid. The place now has a gorgeous bathroom, which I covet. But I do not feel envy. Instead, I feel panicked: I’ve never been able to separate houses from the lives lived in them. In the future of San Francisco that house now represents, I’m the sisters or the beatniks or the hallucinating flower children. That is to say, I’m gone.