I toured a $9 million home in Honolulu to raised perceive the luxurious housing market. I like actual property, and visiting good properties on the market is considered one of my favourite hobbies.
My mother and father are 81 and 78 and stay in Honolulu. Like many individuals their age, they’ve a couple of well being points, and I might wish to be there to assist deal with them.
Since we’re versatile and might stay anyplace, my spouse and I plan to relocate to Honolulu in 2029, as soon as the college entry timing works for our youngsters. There, we’ll take my mother and father to physician appointments, sort things round their home, get them meals, and easily spend extra time collectively whereas we will.
A house buy that far out is without doubt one of the largest monetary selections we’ll ever make, so I am doing what I at all times inform you to do. I am learning the market years upfront. Touring open homes is free schooling. The extra properties you see, the higher calibrated you change into on worth, and the much less seemingly you’re to make an emotional mistake when it is lastly time to purchase.
That is how I discovered myself standing in a 6,700 sq. foot property in Kahala with my spouse, my dad, and our two youngsters. 5 bedrooms, 5.5 baths, a free-form pool with a scorching tub and chilly plunge, a koi pond, and a fitness center with a climbing wall all on about at 15,000 sqft lot.
The home had been sitting in the marketplace for over 200 days, which made it an ideal case research. Who buys these properties? And why was no person shopping for this one?
The Household Verdict Took About Ten Minutes
My spouse’s assessment: it feels too large. She’s proper. We’re a household of 4. Even dwelling in it full-time, we might realistically use a kitchen, a household room, 4 bedrooms, and the pool. The opposite 3,000 sq. ft would exist primarily to be cleaned, cooled, insured, and repaired.
My dad’s assessment was extra sobering. The steps have been troublesome for him. In a single sentence, he eradicated a complete class of properties from our future search. If a part of the explanation we’re transferring is to be there for my mother and father, what good is a pleasant home they cannot comfortably go to or stay in? Any house we purchase wants single-level dwelling for them, and ideally an ohana unit in case a visitor or a caregiver ever wants to remain long-term.
Then there’s the empty nest math no person needs to do. Our youngest heads to varsity in 12 years. Quickly after we might transfer in in three years, it could be two adults rattling round 6,700 sq. ft like two marbles in a shoebox. That is 3,350 sq. ft per particular person, plus an estimated $3,000 to $4,000 a month for the pool, tropical landscaping, and koi pond upkeep, earlier than property taxes and insurance coverage. Name it $150,000+ a 12 months to keep up rooms we might go to like museum reveals.
So the home is a no for us at this value. However the tour raised a greater query. If a household that would stretch for this house finds it impractical, who is definitely shopping for at this value level?
I spent an hour speaking with the itemizing agent to search out out. Her reply was insightful.
“Most Patrons At This Value Level Are Shopping for Second Houses”
Based on her, many patrons of $6-$10 million Honolulu properties do not stay in them full-time. Latest curiosity has come from Japanese nationals and West Coast patrons buying second properties they may use a month or two a 12 months. Given the worth factors, I’ve to think about many are entrepreneurs who had liquidity occasions, as a result of even a $1 million a 12 months W-2 job does not comfortably assist a $9 million trip house.
Let that sink in. Somebody pays $9 million for a home, plus $150,000 a 12 months in carrying prices, to make use of it 30 days yearly. Amortize the carrying prices alone and also you’re at roughly $5,000 per evening of precise use. Then there’s the $380,000 a 12 months in risk-free revenue you can earn off $9 million. So we’re actually speaking extra like $20,000 an evening to stay in the home for 30 days, or $10,000 an evening for those who go to for 2 months a 12 months.
I suppose that is not horrible, particularly if the housing market continues to go up. However that is nonetheless fairly a bit of cash when you may keep at a resort for much much less.
As somebody who spent 13 years working in equities and 17 years writing about cash, I could not compute it. So I stored digging till I discovered the reply to those mega luxurious purchases.
This is what I discovered. The wealthy do not justify these purchases. They’ve merely graduated previous the necessity to.
Justification #1: The Denominator Is Totally different
For our family, an $9 million home would devour too giant a share of our web value. My web value rule for house shopping for says maintain your major residence at 30% of web value or beneath, ideally nearer to twenty%. Violate it and the home begins proudly owning you. So that will imply a minimum of a $30 million web value, and ideally, $45 million.
In case you’re considering of upgrading to a much bigger, dearer house, take a look at my income and net worth requirements to buy a home at all price points. It combines my 30/30/3 house shopping for rule with my web value rule to indicate the minimal and preferrred figures for properties priced from $200,000 all the way in which as much as $50 million. Comply with the information and you will purchase with confidence as a substitute of shopping for with heartburn.
However the typical purchaser of this house is not stretching. They’re seemingly value $100 million to $300 million or extra. At $150 million, an $9 million home is simply 6% of web value. That is the equal of a family with a $1.5 million web value shopping for an $90,000 rental. No one writes suppose items about whether or not that is irresponsible.
The rule I like to recommend is not flawed. Their denominator is simply so giant for the wealthy the rule by no means will get examined. When your own home may burn down uninsured and your life-style would not change, the query “can I afford this?” stops being a query.
The wealthier individuals get, the smaller the share of web value they have a tendency to spend on their major residence. The ultra-rich have the lion’s share of their wealth in companies and investments. The $9 million Kahala purchaser is not breaking my rule. They’re following it to an excessive.
Justification #2: The Home Is A Vault With A Pool
The ultra-wealthy do not consider a trip property property as shelter. They consider it as a retailer of wealth.
Hawaii shouldn’t be making extra land subsequent to the ocean. Provide is completely constrained, world demand retains rising, and trophy properties in world-class areas have traditionally held worth like advantageous artwork, besides you may swim on this artwork.
For worldwide patrons, it is also a foreign money and stability play. A tough asset in a politically secure jurisdiction, denominated in {dollars}, that your loved ones can take pleasure in or escape to if issues go sideways again house.
With the yen having weakened considerably in opposition to the greenback through the years, Japanese patrons who maintain greenback belongings or dollar-earning companies are additionally enjoying an extended foreign money sport than most of us trouble to consider.
The month of annual use is incidental. The home is functionally a bond that occurs to have a lanai. I’ve lengthy argued real estate acts as a bond plus equivalent in a portfolio. The ultra-rich simply take the idea to its logical excessive.

Justification #3: The Property Planning Angle
Whenever you die, belongings included in your taxable property obtain a stepped-up cost basis to fair market value. Purchase the Hawaii home for $9 million, maintain it till it is value $20 million at loss of life, and your youngsters inherit it with a $20 million foundation. In the event that they promote instantly, they owe basically zero capital beneficial properties tax on $11 million of appreciation.
Now, earlier than you conclude the wealthy pay no taxes, the property tax nonetheless applies. In 2026, the federal exemption is $15 million per particular person, or $30 million per couple, with a 40% charge above that. A $150 million property continues to be writing the IRS a verify for roughly $48 million. Hawaii additionally levies its personal property tax of as much as 20% on Hawaii actual property, even for out-of-state homeowners, a element I think half these patrons by no means priced in.
So the step-up is not a tax dodge. It is foundation arbitrage. Rich households intentionally maintain low-basis belongings like actual property contained in the property to seize the step-up, whereas gifting high-growth belongings out early to dynasty trusts. The property tax was going to hit their retained belongings at 40% anyway. The step-up wipes out a long time of capital beneficial properties as a comfort prize.
The home is not only a vault. It is a pre-positioned inheritance, professionally gift-wrapped by an estate attorney all people ought to speak to. Paradoxically, the poorer you’re, the extra essential it could be to get your property so as given probate courtroom is much dearer than distributing belongings by a revocable living trust.

Justification #4: They’re Paying For Optionality, Not Occupancy
I’ve written for years that cash’s biggest return is freedom. That is why the FIRE movement is so enticing to me. I am comfortable to surrender making extra money to have extra freedom. The ultra-rich apply this to actual property.
They don’t seem to be shopping for 30 days of use. They’re shopping for the perpetual choice to get up tomorrow and resolve to spend a month in Hawaii, with their very own sheets, their very own espresso maker, and no person else’s hair within the bathe drain. The empty 335 days do not trouble them as a result of occupancy was by no means the purpose. The flexibility to occupy was.
Is that an insane value for optionality? By my math, sure. However I additionally pay for optionality continually, simply with extra zeros eliminated. We now have a paid off trip property in Lake Tahoe value about $750,000. The precept is an identical. Solely the dimensions offends.
Justification #5: They Do not Do Value-Per-Use Math Like The Relaxation Of Us
This was my closing realization, and probably the most humbling one.
I calculated value per evening. I calculated value per occupied sq. foot post-empty-nest. Then I calculated carrying prices as a share of a protected withdrawal charge.
The ultra-rich do issues in another way. They vibe coded the numbers based mostly on their emotions.
Value-per-use math is a middle-class and mass-affluent survival talent. It is how individuals like us constructed wealth within the first place. However previous a sure web value, the talent atrophies as a result of it now not serves a function.
When somebody value $200 million buys a $9 million home, asking them to justify it’s like asking you to justify shopping for a $12 sandwich. Justify it to whom? It does not matter.
That is the true reply to my perplexity. I used to be asking a query the patrons stopped asking themselves a decade and eight figures in the past.
The Takeaway
In case you’ve ever felt behind as a result of somebody purchased a home that appears impossibly costly, perceive you are seemingly watching a distinct sport with totally different guidelines. The client is not braver or smarter than you. They simply have a denominator so giant the choice required no courage at all.
In the meantime, maintain doing what really works. Tour properties years earlier than you propose to purchase. Convey the individuals who will stay in and go to the house, as a result of your loved ones will spot dealbreakers an inventory photograph by no means will. My spouse wanted one walkthrough to establish the upkeep entice. My dad wanted one staircase to redefine our total search standards.
Preserve working your cost-per-use math. Preserve your major residence at 30% of web value or much less. And earlier than you improve to a much bigger, dearer house, run your numbers in opposition to my house shopping for information beneath.

Being house rich and cash poor isn’t any enjoyable. You’ll seemingly be wired of your thoughts for the primary 12 months for those who violate my information above.
The self-discipline that appears pointless to the ultra-rich is strictly the self-discipline that may get you to their aspect of the desk. And for those who get there, I think you may maintain doing the mathematics anyway. Outdated habits constructed your wealth. No koi pond ought to retire them.
Readers, how do you clarify paying $9 million for a house you employ one month a 12 months? Have you ever ever toured properties method above your value vary to be taught the market? And at what web value, if any, would you cease doing cost-per-use math?
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