A Twist Ending Awaited Two Empty Nesters in San Francisco

After their only child left their suburban Sacramento-area home for college in the Bay Area, Jan and Tony Massara knew what they wanted: a true city living experience.

They knew which city, too.

“There is a spirit, a community, a desire to participate in San Francisco,” said Ms. Massara, 64. “You don’t just observe or live here — you have to be a part of it.”

So in 2017, the couple, nearly lifelong suburbanites who grew up within a mile of each other in the San Fernando Valley area of Los Angeles, gave away almost everything in their four-bedroom home in Granite Bay and rented a two-bedroom apartment in the Inner Sunset district of San Francisco.

It was a drastic life change hastened in part by Mr. Massara’s multiple battles with cancer, which he said are now largely behind him. “It definitely made us think about the future in very different ways,” Ms. Massara said.

The couple, married 41 years after meeting when both lived in the Venice Beach area of Los Angeles, took to San Francisco immediately. But they were in no hurry to buy, with enough financial reserves from Mr. Massara’s career as a bond salesman and Ms. Massara’s work as a corporate underwriting director to rent indefinitely.

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“The goal was, for once in our lives, let’s have some freedom,” said Mr. Massara, 68. “We don’t need to make a decision.”

The pandemic prompted a two-year relocation to the more open wine-country city of Healdsburg, where Mr. Massara could safely wait out the worst of Covid’s risks. But the owner’s impending return meant a hasty move back to the city in 2022, this time to a pricier rental (about $6,250 a month) with 1,400 square feet in upscale Nob Hill.

By mid-2023, San Francisco’s notorious rental market had swung back in the couple’s favor, with national media coverage of crime and homelessness — “the doom loop,” as Ms. Massara put it — driving down prices.

Having fallen in love with Nob Hill, with its easy access to North Beach and Chinatown and transit hubs to everywhere else in the city, they figured they were in a position to strike a better rental deal.

“San Francisco has a bad reputation right now, and with people moving to the suburbs and interest rates so high, prices are down,” said Georgina McInerney, a sixth-generation San Franciscan and the listing agent at Compass for the rental the Massaras took in 2022. “But the smart people are doubling down.”

The couple knew available rentals were abundant, and they quickly found themselves with several options. All were pet friendly, and could accommodate their three cats, with an elevator and a space to park their car.

But it was what they didn’t yet know that would lead them down a new path in their San Francisco adventure.

Among their options:

Find out what happened next by answering these two questions: