In 1984, Kathy Fitzgerald Sherman and her husband, Michael, had the “dumb luck” of buying a condo for $164,000 in Mountain View, CA—Google’s future backyard. Four decades and two trade-ups later, their home is worth $2 million. The rub? By the time their kids were grown and ready to buy homes of their own, they’d been priced out of the market.

When their son, Sam, married in 2018, the computer programmer and his wife rented an 800-square-foot three-bedroom apartment…with three roommates. “It was insane,” Kathy recalls. When their daughter, Leslie, wed five years later, the couples therapist and her husband crammed into a one-bedroom apartment. Both were resigned to rent forever.

That’s when Mom and Dad decided to intervene.

They took their kids and spouses home shopping. Once each couple had found the perfect property, Kathy, a retired lawyer, hammered out a “shared equity” contract where each couple would own a portion of the property. Sam and his wife took on one-third of an $863,725 condo in Oakland; Leslie and her husband one-quarter of an $850,000 condo in San Jose. Mom and Dad paid the rest up front, in cash, leaving their kids with manageable mortgages. Leslie and her husband, for instance, borrowed $200,000 and pay $1,297 per month.

Kids who get homes handed to them often carry a whiff of entitlement. But Leslie thinks this guilt trip is outdated. “We still have this fantasy that we should all be able to buy a home on our own, but it doesn’t shake out that way in modern times,” she says. “This is just the economy.”

Why parents are pitching in on property

In today’s high-priced market, Kathy and Michael are far from the only people who’ve helped their kids buy a house. Nearly 6 in 10 parents have contributed to this purchase or plan to do so. Many view it as an advance on their kids’ inheritance when it can truly make a difference, and the numbers back this up: One study found that owning a home by age 30, rather than 40, leads to a 22.5% higher net worth by 50.

Still, mixing family with real estate can get messy. Since these homes were their investment too, Kathy and Michael didn’t give their kids carte blanche to buy any old house. They put the kibosh on a beautiful Victorian with a bad roof and nonfunctioning HVAC that Sam was eyeing. And since they’ve agreed to pitch in on renovations, they’re not against sharing their opinions on the ROI of upgrades ranging from EV chargers to bidets.

Their advice: The key to keeping the peace is a thorough joint ownership contract, available on co-buying platforms like Joynt or through a lawyer. Kathy’s contracts are 20 pages apiece, outlining every possible worst-case scenario. For instance, if they suspect their kids have dropped the ball on maintenance, they have the right to inspect the property and force repairs. So far, they haven’t had to meddle.

“We’re silent investors. We stay out of it,” Kathy says. “We’ve heard horror stories of parents who share their opinions on furniture arrangements, or have keys and enter unannounced.” Free house or no, “Their kids want out.”

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Most homes are designed to bring the outside in: More glass. More light. More views. But architect Scott Specht at Specht Novak did the opposite by building his own home, the Stealth House, with no windows on its perimeter. Here’s why he thinks windows are overrated.

Q: What inspired you to build a windowless house? “I grew up in a standard suburban home with windows that faced other houses 10 feet away. The blinds were always closed. It never felt like a logical arrangement: Put in windows for light and views, then immediately cover them up. Then add fences and security cameras, and spend a fortune trying to solve problems the windows created in the first place. As I studied architectural history, I became fascinated with the ancient Roman house. They had this figured out: blank walls to the street, with all the light and beauty focused inward on private courtyards. Complete privacy without any of the apparatus we rely on today.”

Q: Where did you build it? “When I found a small alley lot in Austin, TX, surrounded by other houses, the site was practically begging for this approach. A conventional house here would give you windows looking at your neighbor’s siding. Those aren’t views worth framing. So I eliminated them entirely and turned the house inward around two landscaped courtyards with floor-to-ceiling glass.”

Q: What’s it like in there? “The obvious benefits are privacy and no street noise, neighbors, or lawnmowers. But what surprises people is that a windowless perimeter gives you more natural light, not less. Because all the floor-to-ceiling glass faces inward onto courtyards, we get beautiful, dappled light filtered through the branches of the olive tree. There’s also no need for blinds or curtains since no one can look in. The house is inherently secure without any of the technology people normally depend on. It honestly has been a life-changer. There’s this sense of calm that comes over us when we walk in that’s hard to describe. Visitors use the word zen or say it feels like a spa. My wife and I agree that we’d never go back to a traditional layout after this.”

Click here for more of the hidden highs and lows of a windowless house.

Portland, OR, is a tiny home heaven with over 4,200 accessory dwelling units (ADUs). That’s not just a fun fact, but an opportunity, according to Erik Leland at Realty First.

Average home price: $538,687 (down 0.9% YoY according to Zillow)
Homes that sell over list price: 34.5%
Homes that sell under list price: 45.9%
Average rent: $1,717/month

How he got started: A few years out of college, Leland bought a home to live in, then held onto it as a rental after moving out. “That got me hooked,” he says. Since then, he’s purchased over 400 acres of land and a handful of residential properties in the Beaver State, near Sherwood, Lake Oswego, and Beaverton.

The pros: In 2014, Leland’s client purchased a $572,500 property that came with a fantastic bonus: a 1,010-square-foot attached ADU. “He rented out the ADU on Airbnb, generating up to $40,000 a year,” Leland explains. Now, Leland is helping to sell the property for $1,399,000—roughly 144% appreciation over 12 years. “Open houses have drawn interest from people who want it as a mother-in-law suite, as separate quarters for older kids, and as a rental,” he says. “That range of demand is part of what makes a property like this a strong investment.”

The cons: “Oregon has some of the most tenant-friendly laws in the country,” Leland warns. “Landlords need to understand just-cause eviction requirements and rent-increase caps before renting any space.” Rental units also raise insurance premiums, and property taxes are high ($10,350 per year for this property).

His advice: “Evaluate any property as a home and as a future income asset,” Leland says. “My client did not set out to be a real estate investor. He just bought a home he wanted, recognized the potential of the ADU as a revenue stream, and went for it.”

Got a home or housing market you want to highlight in The Playbook? Tell us more about it here, and we’ll consider featuring it in an upcoming issue.