By: Marilyn Olsen

For a long time, the “number” felt like enough.

You could log into a retirement account, glance at the total, and if the line on the chart was moving up and to the right, it was easy to assume the plan was working. Put money away consistently. Stay diversified. Wait.

In recent years, that simple script has felt harder to follow without questions. Inflation squeezed household budgets and changed what future dollars might buy. Interest rate increases shook both stock and bond markets at different points. For many working professionals, the broader lesson was not that long-term investing no longer works, but that a retirement strategy built entirely on market performance can feel distant and hard to control.

That is part of what Matisse Fitzpatrick says he has been hearing more often.

Fitzpatrick is the founder of Generational Wealth Plan, a firm that helps clients evaluate and purchase residential real estate as part of a broader portfolio. His clients, he says, are not typically looking for a dramatic lifestyle shift or a fast bet. The interest is more practical: owning an asset that people understand, with a plan for how it will be operated.

“People are tired of feeling like passengers,” Fitzpatrick said. “When your future depends on things you cannot influence, it can feel exposed. Real estate is tangible. You can see what you own, and you can make decisions around it.”

The Appeal of Ownership, Beyond the Spreadsheet

To understand why real estate comes up in so many retirement conversations, it helps to separate the emotional appeal from the financial logic.

Stocks represent ownership too, legally speaking. But for many everyday investors, the experience of stock ownership is abstract. It lives on a dashboard. It rises and falls with movements that can seem disconnected from daily life.

Real estate feels different because it is physical and useful. It provides housing, which means demand is tied to a basic need rather than a consumer trend. That does not make it risk-free, but it can make the investment feel easier to grasp.

“There is a difference between reading a statement and driving past a property you own,” Fitzpatrick said. “It is concrete. That matters to people.”

The firm’s pitch, he says, is not that real estate replaces retirement accounts. The argument is that for investors who want exposure to something more tangible, rentals can be one way to diversify, as long as the risks are understood.

Income Focus Replaces Appreciation Stories

Real estate has its own history of hype. Many Americans remember the mid-2000s era when speculation was common, and appreciation was treated like an assurance. That story ended badly for a lot of people.

Today, Fitzpatrick says, most prospective buyers he speaks with are less interested in trying to guess where the market will be in a year and more interested in whether a property can function as a stable, well-run asset.

The question becomes less “Will this house double in value?” and more “Can this property cover its expenses, and does the plan still hold up if things go wrong?”

“We encourage people to think about the income first,” Fitzpatrick said. “If a property is underwritten conservatively, and it can cover its costs with room for reserves, it starts to look more like a business than a gamble.”

That framing matters because rental properties behave like small businesses. They have revenue and expenses. They require maintenance. They can lose money in bad months. The operational plan is what determines whether the investment is manageable.

Why Some Investors Focus On Workforce Housing

That operational approach often leads investors toward a less glamorous slice of the housing market.

Rather than luxury condos or high-end vacation properties, many investors look at what the industry calls workforce housing. These are modest homes in the price range that a large portion of renters can afford, often in neighborhoods with consistent demand.

It is not the kind of real estate that shows up in glossy advertising. But the logic is straightforward: affordability tends to drive a much larger pool of potential tenants, and demand can be steadier than in the luxury segment.

In some markets, the firm also works with rentals connected to the federal Housing Choice Voucher program, commonly referred to as Section 8. The program helps eligible tenants pay rent through a subsidy. Landlords who participate must meet property standards, pass inspections, and follow program rules.

Fitzpatrick says Section 8 can be attractive for certain investors because it can bring a structured system to the rental process, but he is quick to add that it also comes with its own administrative requirements and does not eliminate risk.

“Section 8 is not a shortcut,” he said. “It requires compliance, documentation, and patience with the process. It can be a fit for certain people, but they need to understand what they are signing up for.”

Real Estate and Taxes, With the Fine Print

Another reason real estate remains popular is the way it is treated in the tax code, particularly for long-term owners.

Rental property owners may be able to deduct certain expenses associated with operating a rental, and depreciation can reduce taxable income on paper in some situations. Those advantages are not automatic, and they depend on the investor’s specific situation, but they can be meaningful for some households.

Fitzpatrick cautions clients not to treat tax benefits as the core reason to buy. Still, he acknowledges that many investors ask about it.

“People want to be efficient,” he said. “They are not only trying to grow capital. They are also trying to understand how much they keep after taxes. Real estate has rules that can be favorable, but you need competent tax guidance.”

He points to strategies like cost segregation studies and 1031 exchanges as examples of tools investors sometimes explore. Those strategies are complex, and they involve strict rules and timelines. A 1031 exchange, for example, can allow investors to defer capital gains taxes by reinvesting proceeds into another qualifying property, subject to IRS requirements. It is not as simple as “tax-free,” and it should not be pursued without professional advice.

The End of the “Landlord as a Second Job”

Even when real estate looks attractive on paper, many professionals hesitate for one reason: they do not want a second job.

The classic landlord image includes late-night calls, tenant disputes, and urgent repairs. For people already stretched thin, that burden can make real estate feel unrealistic, even if the numbers appear promising.

That is where Fitzpatrick says the industry has changed. Rather than forcing investors into an all-or-nothing choice, a growing number of firms now separate ownership from day-to-day operations.

Generational Wealth Plan’s role, he says, is to help clients source and evaluate properties and establish an operating plan. That can include coordinating renovations when needed and working with property management resources so the owner is not handling every task personally.

“The goal is not to pretend you can own real estate with no friction,” Fitzpatrick said. “The goal is to make ownership practical for someone with a career, a family, and limited time.”

A Necessary Reality Check

It is important to say plainly what real estate can and cannot do.

Rental properties can produce rental income, but there is no assurance they will. Performance depends on tenant demand, local market conditions, property condition, insurance costs, taxes, maintenance, and financing terms. Vacancies happen. Repairs can be expensive. Programs like Section 8 involve inspections and administrative rules that can affect the timeline and rental process. Leverage can amplify gains, but it can also amplify losses, especially if cash reserves are thin.

Fitzpatrick says his firm encourages conservative underwriting, adequate reserves, and realistic expectations. He also tells clients to treat real estate as one piece of a broader plan, not a replacement for every other asset class.

“No one should make decisions based on hype,” he said. “This is about building a portfolio that fits the person.”

A More Balanced Definition of Diversification

The stock market remains a powerful default for retirement savings because it is liquid, accessible, and easy to automate. For many households, retirement accounts will continue to be a foundation.

What seems to be changing is the definition of diversification. It is no longer only about mixing stocks and bonds on a chart. It can also involve combining market assets with tangible assets that operate differently.

For some investors, that means adding real estate exposure through rentals with a clear operating plan and risk controls. For others, it may mean deciding real estate is not the right fit. Either conclusion can be responsible, depending on the person’s situation.

Fitzpatrick says the goal is not to persuade every reader to buy a property. It is to explain why the conversation is shifting, and why real estate has re-entered the retirement discussion for many Americans.

“People want a plan they can understand,” he said. “They want to know what they own, why they own it, and how it is supposed to work.”

About Generational Wealth Plan

Generational Wealth Plan, led by Matisse Fitzpatrick, helps clients evaluate residential real estate opportunities as part of a broader investment strategy. The firm supports property research, deal evaluation, and planning around operations, including traditional rentals and, where appropriate, Housing Choice Voucher program (Section 8) rentals. Real estate investing involves risk, including vacancies, repairs, market shifts, program compliance requirements, and financing constraints. Prospective investors are encouraged to conduct their own due diligence and consult qualified professionals regarding legal, tax, and financial decisions.

Disclaimer: This article is for informational purposes only and does not constitute financial, legal, or tax advice. Real estate investing involves risks, including market fluctuations, property management challenges, and regulatory considerations. Readers are encouraged to conduct independent research and consult with qualified professionals before making investment decisions.