When Blythe Graham-Jones and her husband, Cody Liebman, bought a $635,000 home in East Hampton, the Brooklyn couple’s plan was simple: Kick back there in the off-months, rent it out in the summer, let the property pay for itself.

Nearly one in three personal vacation homes double as rentals—and as the owners’ first forays into real estate investing. Still, as Graham-Jones soon discovered, “renting your own home is a tricky balance.” Here’s why.

Your stuff gets trashed—or stolen

“Things often broke, got stained, or accidentally ‘walked off,’” Graham-Jones recalls about allowing guests into their house. Luckily, “It helped that I had a two-year-old and was expecting our second. I designed the house as chic as I could, but also to withstand toddlers so that it could withstand renters, too. I prioritized washable, durable furnishings. When I did invest, it was in light fixtures and tile that were difficult to mess up.”

To protect their personal belongings, they kept a closet off-limits to guests. “But it was difficult to remember what was there versus what was at home,” she says. “Eventually, we removed all our stuff. It was simpler to pack as if we were going to a hotel versus trying to think through what should stay there.”

It’s hard to relax if you’re renovating

Given that they were aiming for five-star reviews from guests, the couple took out a $250k HELOC to open the floor plan and raise the ceilings…and officially transform their “getaway” into a second job.

“We’d drive out from Brooklyn for a ‘vacation’ with our kids, but use that time to cram in projects or line up hours of contractor meetings,” Graham-Jones says. “My husband certainly didn’t want to spend the weekend painting or picking up furniture, but I got him to do it anyway. We’d often drag my parents or others in on projects, too.”

You might also be torn between designing for yourself and for your guests. How she deals: “When we’re renovating a property, my husband and I decide ahead of time: Are we renovating to maximize resale value, or how much we can rent it for, or to make me like it the most? The best projects have one single-minded objective. If you’re trying to do all three, you’re going to water them all down, unless you have a limitless budget.”

But these compromises eventually pay off

In 2026, the couple sold the first house for $1.95 million—triple what they paid nine years earlier. Graham-Jones also quit her job in advertising to transition from weekend warrior to full-time flipper. Her success even inspired her mother and mother-in-law to turn their own family properties into Airbnbs. However, “the way renters moved things around in the kitchen initially drove them nuts!” Graham-Jones says. “They eventually became more immune. I’m fully detached from it, because I’ve decided the benefit of rental income is more important than the nuisance.”

And despite the messy boundaries, she thinks homeowners who open their homes to guests bring something extra. “You can feel the difference when you rent an Airbnb that the owner has never set foot in,” Graham-Jones says. “The houses that have been loved by the owners are the ones that are actually the most enjoyable to stay in. This is why, when we’re setting up a new property as a rental, we stay in it for a month or so to work out any kinks.”

🪴 Move over, minimalism and maximalism. Today’s chicest design trend is midimalism.

America’s best place to live today is a “little utopia” we’ll bet you’ve never heard of.

Super El Niño is coming—and it could make these eight states “uninvestible” by summer.

A $1,000 home in Lake Tahoe? No, that’s not a typo, but there is a catch.

The House of Representatives approved a bill that limits how many homes big investors can buy—but there’s good news, too.

How one investor turned a $630,000 building into an “autopilot cash flow machine.”

The secret to their 40-year marriage: eight gut renovations. Take a tour inside the homes of these serial renovators (and the one upgrade they regret).

Data center developers spent years hunting whales. Here’s why that era may be over.

🤏 Odds are you can’t afford to buy a resort…but we’ll bet you can purchase this adorable alternative.

Summer’s hottest rental market—with high rents, low vacancies, and fierce competition—isn’t New York or San Francisco. This scrappy “Creative Capital” just stole the crown.

In real estate, a great listing photo sells the house. For Amanda Lesser’s pooch, Maddy, it launched a career. After crashing the first shoot uninvited, this photogenic canine has appeared in over 60 listings represented by Amanda and Bruce Lesser of The Dad/Daughter Team with Remax Accord. Amanda explains how pets could help you fetch a higher price.

Q: How did Maddy first appear in your listings? “Her first appearance was an accident, actually! Our photographer just started clicking away while Maddy was perched on a sofa, and we decided to use those photos in the listing.”

Q: How did buyers respond? “The response was so pleasant from buyers that we decided, ‘Let’s keep doing this!’ Maddy has appeared in over 60 listings since her first accidental photo shoot.”

Q: What are the benefits of featuring pets in listings? “I think she keeps viewers engaged to look at all of the photos from start to finish. Whether or not that sells the listing, I couldn’t say, but she may help capture someone’s attention long enough to notice details that interest them rather than rushing onto the next listing.”

Q: What advice do you have for other sellers who may want to try this trick? “With listing photos that include pets, remember that the home is what you’re really showing off. So proper home prep is most important, and the pet should be just a cute accessory.”

Pristine beaches. Posh clientele. The Hamptons, a group of towns on the eastern end of Long Island, has earned its reputation as New York’s swankiest summer escape. But Blythe Graham-Jones, who has bought seven properties in the area and documents her renovations on her Instagram account, blythebuilds, swears the market is less intimidating than it seems.

Median sale price: $1,675,000 (+13.6% YoY according to Redfin)
Median time on market: 116 days (+19 days YoY)
Homes sold above list price: 14%
Median rent: $35,000/month (East Hampton only, per Zillow)

The pros: The Hamptons command insane rents from Memorial Day through Labor Day, which can zero out a full year’s carrying costs. “If you’re looking for a hybrid second home/rental property, the Hamptons is uniquely great because you can use it personally for nine months without losing out on much rental income,” Graham-Jones explains.

The cons: For rents this high, guests have zero tolerance for ants in the kitchen or a lukewarm pool. “You can’t charge $20k+ a week and expect no complaints,” Graham-Jones points out. This means your housekeepers, pool vendors, pest control, and plumbers had better be happy to pick up the phone and make house calls on the Fourth of July. Plus, most Hamptons townships enforce strict rules on minimum stay requirements (typically two weeks), occupancy limits, and parking, and impose harsh penalties for noncompliance (think: $15,000 fines and even prison time).

Her advice: Choose your area carefully, as this can affect what’s allowed in your rental. South Hampton (which includes Hampton Bays and Sag Harbor) doesn’t allow rentals of under two weeks. But East Hampton (Amagansett, Wainscott, Springs, and Montauk) allows two rentals of under two weeks every six months. “This can drive up rental income significantly,” explains Graham-Jones, who sticks to homes in this area.

And for the record, “The Hamptons” is considered anything on the South Fork of Long Island from Westhampton to Montauk. For deals, there is a back door: the North Fork, where comparable properties can be found for 20% less. Just know that this is not technically the Hamptons, and it will rent for about half the rate.

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.