I’m going to try something a little different today. Stay with me.
A few years ago, after nearly a decade of casual searching, my wife and I finally bought a property outside the city. It had a gut-punch western view of the bay and mountains beyond—sunsets every night, plenty of yard and gardens, a quiet neighborhood with a real sense of community, and low crime.
The house itself? A World War II relic with questionable insulation, failed windows, too many insects, no garage, no primary bedroom, and a long, awkward layout. Multiple architects and builders advised us it would be cheaper— and smarter— to tear it down and start fresh.
No problem. That was the plan. The land was gold, and we had both time and a realistic construction budget.
We spent the winter there, riding out a cold snap that put frost not just on the glass but around the windows. Summer came and we frequently couldn’t cook— no AC, no kitchen ventilation. Still, we pressed on.
Over time, we worked through maybe 13 sets of architectural plans. We built mockups, created elevation drawings, and installed three rounds of “story poles”— essentially a skeletal lumber outline of the proposed house— so neighbors could preview the end result.
Because here’s the catch: we were in an HOA. And the board had to approve our plans, guided by community feedback. The biggest concern? “Don’t block my view.” Not even a sliver. Neighbor sign-off was required.
We weren’t looking to build bigger, just better. Improve the layout. Tuck a garage into the hillside. Fix a treacherous driveway. Preserve everyone’s sightlines. My wife visited nearly 50 neighbors— four times the required number— to build support (you don’t want me in that role). She nurtured those relationships for months.
The process dragged on for a year and a half. Twice we presented to the board and twice we were shot down, each time revising the plans and story poles to further reduce the visual impact.
Finally, in November, it looked promising. We had the signatures. We had the votes. We were there.
Then one neighbor— farther away and less affected than most— derailed it. He complained, shouted, insulted us, made it personal. No one backed us. Not even the board members who had pledged their votes. We lost.
We regrouped and explored renovating within the home’s existing footprint, which was grandfathered. But that long, narrow shape didn’t work. We had a killer location and a crummy house— and after two more years of stress and cash, the best we would get was “fine.” So we bailed.
We sold the house quickly, a hair above asking. Net of mortgage interest and selling costs, we essentially broke even.
We moved just a few houses away into a nicely remodeled rental. It has insulation, new windows, AC, a fancy kitchen and bathrooms, privacy, greenery, a two-car garage with storage, a huge covered deck— and still a great view.
You know what? It’s terrific.
Loved ones visit and stay. We host friends for sunsets. We garden. We sleep bug-free. We’ve got space for Costco hauls and sports gear. When something breaks, we call the landlord. We’re comfortable.
Why am I telling you this in my investing column? If you’ve come this far you might be ahead of me, because here’s what happened next: I reinvested the equity from that home— down payment and appreciation— into the stock market.
That money had appreciated around 7% per year during our brief ownership. But if my historical average investment returns hold, that capital will now compound faster— working for me in the stock market, where I make my living.
And that’s the actual point of this piece.
We owned our residence for over 30 years. I never questioned it. Why would I? “Grownups buy houses.” “Homeownership builds wealth.” It’s what our parents and grandparents did. When we married, it never even occurred to me not to buy.
But I’m rethinking that assumption.
Urban property is complex and costly. It’s illiquid, high-maintenance, complicated and awkward and slow to transact, and heavily taxed. Stocks, by contrast, are liquid, low-maintenance, and favorably taxed if held long-term. So why do we push people toward homeownership?
We hear about “forced savings”— that even if you’re not a disciplined saver, your home builds equity, and you get the full appreciation on borrowed capital. There’s the mortgage interest deduction. And the supposed security of “owning your own home”— though tell that to anyone who got foreclosed in 2008.
I’ve run the numbers. Stress-tested the logic. Even after factoring in tax breaks and equity gains, for me, the financial case for homeownership is not obvious.
Sure, I miss the pride of ownership. But I’ve gained peace of mind. I take pride in my rental. I’ve got no surprises, no repairs, way more financial flexibility. Where I live in Washington State, tenant protections are strong. It’s only been a few months, but so far, it’s a good trade.
Sometimes, despite your best efforts, things don’t go your way. You play by the rules— and still lose.
That’s when it’s worth asking: Whose rules are you playing by? Maybe it’s time to change the game.