In many booming white-collar cities, such as Palo Alto, with its median property value of $2.5 million, even six-figure earners struggle to find affordable housing. Photograph by Marcio Jose Sanchez / AP

I spent the nineties growing up in San Francisco, which, like many cities in that decade, churned with swirls of startling change. Boulevards were beautified (although a shaggy indie scene managed to thrive on side streets). Coffee changed from canteen sludge to crisp black java, and still cost less than a sandwich. New museums opened. Trendy people pursued “desktop publishing” in warehouses long left to rot. Urban life means riding a pendulum between extremes: a city is always en route to being either a gritty nightmare or a bourgeois snooze. But, for a year or two late in the decade, San Francisco seemed to feel like many things to many people. Starter homes turned into desired properties. Middle-class homeowners unexpectedly woke up house-rich. For those lucky enough to avoid the era’s darker spectres—AIDS, an early wave of rental evictions—the nineties often brought the winning ticket in a lottery they hadn’t meant to enter.

Today the winnings have been paid out, and the landscape of local concern has changed. In this magazine, I’ve written about the housing and inequality challenges facing the Bay Area and the nineties nostalgia haunting much of San Francisco’s current growth. The city’s long-held notion of itself as a home to the progressive middle is harder and harder to sustain. As in many quarters (think of Brooklyn), living on a normal salary—the type available outside tech or some similarly well-heeled industry—is getting hard. The quandary became flagrant last week: news circulated that the Palo Alto City Council had moved to explore subsidized housing for families earning between a hundred and fifty thousand and two hundred and fifty thousand dollars a year.

The proposal, advanced by Palo Alto’s vice-mayor, travelled far and wide because the numbers seemed preposterous. In much of the country, two hundred and fifty thousand dollars a year qualifies as wealth. The subsidized-housing idea has an eye to public employees—government officials, teachers, firefighters—and would be part of a constellation of housing efforts that the council has launched to build units in Palo Alto’s downtown, near its transit hubs. This has the admirable goal of reducing car emissions but the amusing implication that households earning a mere quarter of a million a year are unlikely to be able to afford a car. Palo Alto’s median family income has been marked at $167,408, the third-highest in the country for a city in its size class. The median property value in town, according to Zillow, is two and a half million dollars and on the rise. The council’s plan to help the area’s struggling six-figure earners is, by a certain logic, sane.

So sane that Palo Alto hasn’t been the first Bay Area city to entertain the thought. The possibility of subsidizing housing for the middle class has bounced around greater San Francisco for a while. When I spoke, in 2014, with Ron Conway, a generous donor and a private adviser to San Francisco’s mayor, he championed the idea of letting San Francisco’s middle class take shelter in subsidized housing (with a cutoff of $145,650 for a four-person household) to be built in large part in the city’s Candlestick and Bayview-Hunters Point neighborhoods. The sell was hard, in part because those areas had been the scene of up to half of San Francisco’s homicides and abutted a shipyard not yet fully cleaned of toxic and radioactive waste. Still, a version of the plan is going forward.

What does it mean to redefine the urban needy upward? One of the chief risks facing booming white-collar cities, such as San Francisco and New York, is that the new poor will supplant the old in public concern. Palo Alto, for all its wealth, is also touched by destitution: fifteen per cent of the population is below the poverty line in parts of the city, and in neighborhoods just outside the city limits that number approaches thirty-five per cent. Close problem-solving attention is required. A self-sustaining middle class frees up local support mechanisms for people who would struggle anywhere they lived.

The most common argument in support of affluent growth in cities is a trickle-down one, but what’s supposed to trickle down is less money than opportunity. Metropolitan regions such as New York and the Bay Area right now can make demands. The best and brightest seem to want to live and work there. They bring money, mechanistic know-how, and, most important, other best-and-brightest types, equipped with an impressive range of skill.

The pressure to subsidize the middle class by civic accommodation indicates that something, in the Bay Area, at least, is not merely unequal but out of balance. Opportunity isn’t trickling down as it should; the efflorescence of creative talent and technological skill under way hasn’t yielded much beyond a few established channels of success. Some observers have begun to note a faltering in the service market that was designed to empower the local middle class. It has become clear that the American Dream needs roadwork: there are unpaved gaps in the route between subsistence and prosperity.

Palo Alto and the surrounding demesnes—mostly sunny, rich, and liberal—are not often thought to reflect the plight of the great American middle. But, in the cost-of-living context, the odd class-warping going on in Palo Alto seems to find a place among broader concerns. Candidates in both major political parties gain support with promises of escape from a defunct-seeming socioeconomic order. A sense of failing systems is widespread. Perhaps ironically, no sustainable solution has yet emerged even in the nation’s capital of innovation. That’s ideologically awkward for the tech industry, which sees itself as a meritocratic accelerator. If someone near the top of the pay scale in his or her field—say, a teacher—can’t afford to hang around, the meritocracy has been corrupted. To be a middle-class person living in subsidized housing is uncomfortable, not because you didn’t earn it but because, actually, you’re pretty sure you did.