Ever since she left her parents’ farmhouse in Ontario, Canada, in the late 1990s to study design in Toronto and then New York, Mara Ambrose has been open to change — including changing her mind.

When she was in her 20s, a six-month European trip with friends became a decade-long stay, complete with British citizenship and the purchase of a two-bedroom flat in London. An impulsive enrollment in a wine class there led to a career shift, from design and photography to enology and viticulture.

All of that eventually led Ms. Ambrose, now 44, to Northern California, where her experience in England’s sparkling wine industry paid off in a series of jobs making the same kind of wine for Napa Valley and Sonoma Valley vintners. With the pace of her work and the demands of the harvest, Ms. Ambrose was spending less time in London. By the summer of 2022, she had sold the flat at a profit — but where to invest the money?

“I had about $400,000 just sort of sitting,” Ms. Ambrose said recently in the sunny dining room of a Napa home owned by her partner, Matthew Rorick, 52, a winemaker with whom she lives and works. “My financial adviser said, ‘You have way too much cash. You need to do something with it.’”

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During a business trip to Vermont last summer, the couple fell in love with the area. Its proximity to her parents in Canada was also appealing. An online search led Ms. Ambrose to their “dream property” on 82 acres, but her offer was rejected — “a devastating blow,” she said.

By then, the idea of investing in real estate had taken root. And California was calling. Her new plan: buy a house and rent it out.

Mr. Rorick and his father own rental properties and primary residences in Napa, a city of about 80,000 in the heart of the Napa Valley wine region, and their experience made it easier for Ms. Ambrose to envision buying a place she wouldn’t be living in.

“I had to switch up and think like a renter while looking at houses,” she said.

She was open to buying either in the city of Napa or in Sonoma County, to the west, which is generally less expensive. Her budget was around $700,000, and she wanted to charge enough rent to at least cover the mortgage payments.

“Napa is a tough market,” said Kari Pryatel-Tucker, of Homestead Real Estate, who began working with Ms. Ambrose in July. “The median price point is $925,000, and we are always searching for new inventory. There is very little room for new development here — you’re surrounded by vineyards.”

And there was another pressure: Harvest was fast approaching at Mr. Rorick’s ranch and winery in the Sierra Foothills. If Ms. Ambrose didn’t buy a place by mid-August, the search would have to wait.

Among her options:

Find out what happened next by answering these two questions:

Mark Kreidler

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