I’m a Supercommuter. Here’s What It’s Really Like.

Sometimes I sleep in a different New York City hotel room every night.

On a recent Monday, it was a Midtown Manhattan Hampton Inn. The next night, a budget hotel downtown. Then I moved to a Hyatt in Queens, near John F. Kennedy International Airport, where I waited to check in behind a group of pilots and flight attendants.

The reason for this madness: My job is in New York, but my apartment is in Columbus, Ohio. When hotel prices are high, I property-surf to find a lower rate.

For more than a year, to the bafflement of family, friends and colleagues, I have attempted to live and work as a supercommuter. What began as a postpandemic experiment of flying to and from New York each week has turned into what I am hesitant to call a lifestyle.

Like many, I moved out of the city early in the pandemic, relocating near family in the Midwest. When it came time to return in 2022, I was underwhelmed at the housing options in my price range. I toured one-room studios facing brick walls and climbed crumbling staircases to reach dank apartments with ancient fixtures. I also had grown accustomed to midweek evening walks with my sister in Ohio, and a short drive to see my parents. I didn’t want to fully give that up.

Using back-of-the-envelope math, I thought I could keep my expenses—rent in Ohio, plus travel costs—at or below the price of a nice New York studio, or roughly $3,200 a month. The Wall Street Journal requires office attendance at least three days a week and, since I commute by choice, I pay all my travel expenses.

Luxury suites and room service

The challenge felt oddly thrilling. If anybody could find a way to subvert high New York real-estate costs, while remaining close to family, I thought it might be me. For years, I’ve been an on-call travel guru to friends and co-workers, coaching people on how to navigate flight cancellations and play the credit-card bonus games. I memorise aircraft configurations and spend hours reading mileage blogs and industry sites like Airliners.net.

Before mileage runs became useless, I obsessed over reaching top-tier airline status by spending as little as possible. (Family members still roll their eyes at the six hours I spent in Anchorage one December afternoon to requalify for Delta’s Diamond tier.) When a flight is oversold, I am quick to volunteer my seat in exchange for a voucher. (My best-ever haul: $2,000 after giving up my seat on multiple oversold flights one Saturday in San Francisco.)

Nerding out about this stuff has allowed me to travel farther and in more rarefied air than I could otherwise afford.

Entering my supercommuter era, I had visions of flying to New York on a weekday morning (8,500 points one way on American Airlines), spending the day meeting sources and filing stories, and retiring to one of my favorite points hotels—the Beekman. Mornings would begin with a free breakfast thanks to my Hyatt status, before a short subway ride to the office. After two nights, I’d return to Columbus and my roomy apartment, half the price of a Manhattan studio.

Shocking no one, that fantasy soon came crashing down.

Burning points on fancy hotel rooms was the first problem. The life of a journalist is hard to predict. I repeatedly found myself on deadline and having to rebook flights or stay an extra night, costing me money or miles.

Once I was back in the city, it also got harder to say no. Stay an extra night to attend a friend’s birthday party or meet a CEO in town just for the day? Sign me up. I didn’t want my living situation to strain relationships or interfere with my job, which I love.

To conserve hotel points, I swapped the Beekman’s elegant rooms in lower Manhattan for a Hyatt attached to a casino in Jamaica, Queens. My rooms overlooked a sea of empty parking spaces, but required half as many points as Manhattan alternatives.

Flight delays and blown budgets

By summer, with my miles dwindling and New York hotel rates rising, I reluctantly began to rely on the kindness of those around me. Hearing I might need a place, one friend mailed me the keys to her family’s unoccupied apartment in New Jersey. Another let me stay in her smartly designed Brooklyn one-bedroom for weeks as she traveled. A cherished deskmate, known for her tell-it-like-it-is demeanour, repeatedly offered a bedroom in her Chelsea loft, handing over the keys with a sometimes expletive-tinged reminder to: “Get a f—ing apartment.”

I watered plants, walked friends’ dogs and fed their cats while they were away. Still, working in a city without a permanent home took a toll. I came to dread the go-to question asked at parties and work events in New York: “So where do you live?”

After house sitting for friends, I fell in love with some of their pets, including my friend Vanessa’s Border Collie mix, Ivy. But when in hotels without a refrigerator or stove, uninspiring meals abounded; a late-night dinner of yogurt and fruit.
CHIP CUTTER/THE WALL STREET JOURNAL

If I admitted, “it’s kind of complicated,” I got sucked into explaining my life as a supercommuter. Sometimes, I’d just tell people the location of that evening’s hotel. (Chelsea!)

Costs mounted in the fall, New York’s prime tourist and business-travel season. Friends teased me for embracing a life of chaos. They weren’t wrong. Without a refrigerator or stove, late-night dinners often consisted of yogurt and fruit purchased from a 24-hour CVS. Needing to pack light, I stored shoes under my desk and left spare outfits on an office coat rack.

To get to the office on time, I set my alarm in Columbus for 4:15 a.m. and hustled to the airport for 6 a.m. flights. When everything went according to plan, I made it door-to-door in three hours. If delays occurred, I scrambled to rebook on other flights.

My obsessive tracking of New York hotel prices taught me that dynamic pricing isn’t reserved for airlines. Hotel costs can fluctuate half a dozen times on the check-in date, so instead of booking in advance, I’d wait to pull the trigger until 10 p.m. some days after the rates fell.

In the end, the math didn’t work. I blew my budget by 15% and drained my miles balance. But I flew so much and stayed in so many hotels that I kept my elite status with Hyatt and American.

I still enjoy having one foot in the Midwest and one on the East Coast, though I’m not sure how long I can keep it up. I’m writing this from Columbus, where I overlook a beautiful park outside my picture window. My lease is up, but hotel rates in Manhattan this winter have plunged now that the holidays are over. Maybe that New York apartment search can be put off a little longer.

Happy is the family whose members—parents, grandparents and grown children—trust each other enough to cooperate on shared goals, especially financial ones. When that is truly the case, Uncle Sam’s tax rules can help as well.

This matters especially now that mortgage rates are above 7%, and many families are looking for ways to help younger members. If the elders have resources and are confident younger ones can cooperate, a family loan could make homeownership possible while providing the elders with a useful income stream.

Other strategies can actually lower taxes, such as when funding 529 plans or Roth IRAs, or when someone inherits a traditional IRA with required withdrawals larger than they will need.

Here are three strategies useful for functional families.

Intrafamily loans

It is perfectly legal for families to lend money to a relative for a down payment or even a private mortgage.

But it is important not to cut corners, says Ryan McKeown, a CPA with Modern Wealth Enhancement in Minnesota. If the loan is for a down payment, be honest with the mortgage provider and have a formal agreement. The lender owes tax on the interest payments received.

If the loan is for a private mortgage, both sides should have legal representation with a formal written agreement, including payment terms. The lender owes tax on the interest, and the borrower often can deduct it if he or she itemizes.

To avoid IRS trouble, the interest rate shouldn’t be lower than the agency’s Applicable Federal Rate at the time of the loan. Currently that is about 5% for loans longer than nine years; about 4.5% for loans three to nine years; and about 4% for loans three years or less. Currently, traditional mortgage rates are generally above 7%.

In addition, the lender could use the $19,000 annual gift-tax exemption (described below) to forgive some or all of the interest or principal annually. If both lenders and borrowers are married, that is up to $76,000 a year. There is no tax for the borrower on such forgiveness, because it is from a gift.

If you’re going this route, McKeown advises against having a fixed plan to forgive the debt. Instead, do it in one-off letters specifying the amount—and keep careful records. Otherwise the IRS might try to treat the loan as a taxable gift.

Asset gifts

Powerful tax-saving moves for families often use gift-tax provisions. Under current law, anyone can give anyone else up to $19,000 of assets annually, free of gift tax. That means a married couple with three grandchildren could give them a total of $114,000 in 2026.

The gifts can be cash or other assets, like stock. For noncash gifts, the cost basis—which is the starting point for measuring taxable gain after a sale—“carries over” to the recipient. So if someone buys $1,000 of stock and gives it away when it is worth $5,000, the recipient’s cost basis is $1,000. If the recipient later sells the shares for $8,000, the taxable gain is $7,000.

Here’s an example showing how gifts could save a family taxes. Grandma is a widow of modest means, while her child and spouse have prospered. The couple has two children, and they want to contribute $5,000 to a 529 college-savings plan for each—but they need to sell stock to do it. Their tax rate on the sale would be 18.8%, and they would need to sell about $11,000 of stock.

However, Grandma’s federal tax rate on the stock sale is 0%. If the couple gives $10,000 of shares to Grandma, she could sell them, pay no tax, and fund the grandchildren’s 529 plans. This saves about $1,000 of tax.

These moves are legal, and they could be used in other ways, such as to help a young person fund a Roth IRA.

But trust among family members is essential: Under the law, givers can’t put conditions on a gift. Grandma could use her stock proceeds to take a cruise, but she makes 529 contributions instead.

Mark Sellner, a retired tax attorney and CPA living in Sarasota, Fla., uses this strategy. His children sell stock he gives them and fund 529 plans for his grandchildren.

The family’s tax savings aren’t huge, but he likes other benefits. The sales by his children don’t boost his adjusted gross income, which in turn could raise his Medicare Irmaa premiums or his 3.8% surtax on net investment income.

Sellner doesn’t worry about his children using the funds for another purpose.

“There can’t be any strings attached to gifts. Of course, it is up to us to decide whether to make them in the future,” he says.

Two caveats: The “kiddie tax” applies to most children under age 24, and it is levied at the parents’ rate on investment income above $2,700 in 2026. Consider this before making gifts to a young person.

Investors who give away stock also forgo the step-up, an important provision that exempts assets held at death from capital-gains tax.

Sellner knows he’s losing a step-up, but says, “The children could use a little more now. Why should they wait 20 years to get it?”

Disclaimers

A disclaimer is a highly useful strategy in which one heir renounces an inheritance in favor of another heir. Assuming family members cooperate, this can save taxes.

Here’s one example. Dad died and had a large traditional IRA that he left to Mom. She has enough assets and income to cover her expenses, and she lives in a state with a stiff estate tax. The inherited IRA would put her estate over the threshold.

Also surviving are three young-adult children. If Mom disclaims all or part of Dad’s IRA within nine months of his death, that amount could go directly to the children. They will have 10 years to empty the account, and the family as a whole will likely save estate and income taxes.

Disclaimers have many key details, especially regarding beneficiary documents. Although heirs have great freedom in choosing what assets to disclaim, the rules about who gets disclaimed property are rigid. It is best if the original owner names tiers of heirs so that if one disclaims, the next recipient is clear.