Work Checks to Play Checks
Real estate has long been one of the most reliable paths to building wealth. It offers income, tax efficiency, and appreciation. But not all real estate income is created equal. Some checks are earned quietly. Others are earned the hard way.
This is a story about two longtime friends—both successful real-estate owners—who took very different paths.
Two Owners. Same Assets. Different Outcomes.
Both men owned a mix of rental homes and small commercial properties. Both understood leverage, depreciation, and the tax advantages of real estate. Both had built meaningful net worth over decades.
But as time passed, their experiences began to diverge.
One of them—my client—decided several years ago to sell his properties and complete a 1031 exchange into Delaware Statutory Trusts (DSTs). The other chose to continue managing his properties himself.
At first, the difference wasn’t obvious. Rent checks were still arriving for both of them.
Over time, however, one set of rent checks began to feel less like income—and more like compensation for labor.
When Rent Becomes a Job
As his properties aged, my client’s friend found himself working more,not less.
A tenant of nearly 20 years eventually moved out. What followed was a costly renovation:
- A new roof
- Plumbing updates
- Appliances
- Electrical and cosmetic repairs
To save money, he did much of the work himself. Weeks turned into months. Golf days were replaced by repair days.
When new tenants finally moved in, they weren’t like the first. Rent payments were missed. Damage occurred. The tenants left. The property sat vacant for months and required additional repairs before it could be marketed again.
The rent checks—when they arrived—were anything but predictable.
They were work checks.
A Conversation on the Golf Course
One afternoon, while playing golf together, my client listened as his friend vented about vacancies, repairs, and the time and money being poured into a single property.
That’s when my client said something that stuck:
“Those aren’t rent checks. Those are work checks. And they’re not very steady ones.”
He went on to explain the difference.
“What you need,” he said, “are play checks.”
What a Play Check Looks Like
My client’s DST income arrives whether he is:
- On the golf course
- Traveling in an RV
- Spending time with his grand kids
- Working in his wood shop
The income is not dependent on tenants calling, roofs leaking, or insurance renewals. There are no capital calls. No surprise repairs. No tracking expenses. No phone calls.
Most importantly, there is no requirement to trade time for income.
Addressing the Skepticism
His friend was skeptical at first. After all, the reason he invested in real estate was tax-efficient income.
He liked:
- Depreciation
- Expense write-offs
- Owning tangible assets
My client explained that none of that changed.
With DSTs:
- He still owns institutional-quality real estate
- He still receives depreciation and tax deferral
- He still completed a valid 1031 exchange
- He now benefits from non-recourse financing and trust-level liability protection
- His tenants are typically investment-grade and A-rated
The difference is not the asset class.
The difference is the workload.
Predictable Wealth. Predictable Retirement.
Real estate remains one of the most predictable ways to build wealth overtime.
DST real estate is one of the most predictable ways to retire from the work.
No property taxes to escrow.
No insurance policies to shop.
No repairs to manage.
No tenants to chase.
Just income designed to show up whether you are working—or not.
The Real Question
At some point, every property owner faces the same decision:
Do you want your rent checks to compensate you for labor?
Or do you want them to fund your life?
The difference between a work check and a play check is not real estate.
It’s how you own it.
*Colorado Financial Service Corporation and its affiliates do not provide tax, legal or accounting advice. This material has been prepared for informational purposes only, and is not intended to provide,and should not be relied on for, tax, legal or accounting advice. You should consult your own tax, legal and accounting advisors before engaging in any transaction.


