For many older adults, real estate represents one of the largest sources of wealth they will ever own. A longtime family home, a rental property or a portfolio of investment properties can provide financial security—but those properties can also create complicated decisions as retirement approaches and families begin planning for the future.
In this three-part series of Answers for Elders, host Suzanne Newman talks with Cory Boldroff, a certified senior real estate planner, about the unique challenges seniors and their families face when managing, selling, downsizing and transferring real estate. Cory’s focus is helping families build, protect and transfer generational wealth through real estate, while developing strategies for the next transition.
The three-part conversation covers everything from making a senior move less stressful to evaluating investment properties, understanding 1031 exchanges and exploring Delaware Statutory Trusts (DSTs).
Senior Moving and Downsizing: Planning Before a Crisis
The first part of the conversation begins with an issue many families eventually face: moving after decades in the same home.
For an older adult who has lived in a home for 30, 40 or even 50 years, moving isn’t simply a matter of packing boxes. The home may contain memories of raising children, a marriage, family celebrations and important chapters of life. Leaving can be emotionally difficult even when the move is ultimately the right decision.
Cory explains that families don’t necessarily have to manage every part of a senior move themselves. A senior move manager can coordinate packing, organizing, decluttering, moving and setting up the new residence. In some cases, the senior can even participate in designing the layout of the new home before moving in.
That kind of support can be especially valuable when someone is moving to senior living. Rather than having an older adult live among boxes while everything is being unpacked, families may be able to arrange temporary accommodations while the new residence is prepared.
One of the most important messages from the discussion is to plan before a crisis occurs. Downsizing doesn’t have to happen in a frantic weekend. It can take months or even years, with one room addressed at a time.
Cory also encourages families to be realistic about belongings. Some items may have significant sentimental or monetary value, while other possessions may simply need to be donated, removed or given away. Hiring professionals to handle the difficult work can reduce the physical and emotional burden on an older adult and their family.
The goal isn’t simply to empty a house. It’s to make the transition into the next stage of life as manageable and dignified as possible.
Investment Property Planning: Is Your Real Estate Still Performing?
Part two shifts from the family home to investment properties and real estate wealth. Owning a rental property can seem like an obvious success. Perhaps the mortgage is paid off and the property generates monthly income. But Cory challenges listeners to look beyond the amount of rent being collected and ask a more important question: Is the property actually performing well relative to its current value?
The conversation introduces several factors investors should consider, including cash flow, cap rate, cash-on-cash return, appreciation, taxes, insurance, maintenance and financing.
A property that once made excellent financial sense may no longer be the best use of the owner’s equity years later. As Cory explains, the value of a property can increase dramatically while its rental income remains relatively modest. That can create an important planning opportunity. Instead of simply holding a property because it has always been part of the portfolio, an owner may want to periodically evaluate whether the property is still meeting their financial objectives.
For older adults, this becomes particularly important because managing rental property can eventually become burdensome. Repairs, tenants, maintenance and property management don’t necessarily get easier with age.
Understanding 1031 Exchanges
The second episode also introduces the 1031 exchange, a strategy discussed in the program for potentially deferring capital gains taxes when an investment property is sold and qualifying replacement property is acquired.
Cory emphasizes that there are important rules and deadlines associated with a 1031 exchange. The discussion specifically addresses the need to identify replacement properties within the required identification period and complete the purchase within the applicable timeframe.
The conversation also stresses the importance of having experienced professionals involved. A mistake in the process can have significant tax consequences.
For anyone considering selling an appreciated investment property, the takeaway is simple: don’t wait until after the sale to start thinking about taxes and replacement property. Planning needs to happen before the transaction is completed.
Because tax laws and individual circumstances vary, listeners should consult qualified tax, legal and financial professionals before acting on any strategy discussed in the program.
Delaware Statutory Trusts: An Option for Investors Done Being Landlords
The final part of the series addresses a particularly interesting situation: What if you still want exposure to real estate but no longer want to be a landlord?
Cory introduces Delaware Statutory Trusts, or DSTs, as one potential strategy for certain investors. The discussion focuses on how a DST may allow an investor to exchange an active property interest for an interest in a larger real estate investment while reducing the day-to-day responsibilities associated with owning rental property directly.
The example discussed in the episode involves larger commercial properties that individual investors might not ordinarily be able to purchase on their own. Instead, investors can participate by owning an interest in a trust structure.
The appeal for some older investors is the potential for a more hands-off approach. Rather than receiving a call about a broken light bulb or dealing with a tenant problem, the investor isn’t managing the property directly.
The episode also discusses how DST interests can potentially be incorporated into a 1031 exchange and how fractional ownership may provide flexibility when thinking about inheritance and generational wealth.
For families with multiple heirs, direct ownership of several properties can sometimes create complicated decisions about who manages the properties, who receives which property and what happens if siblings have different financial goals. Cory explains that a DST structure may offer different possibilities for dividing interests among beneficiaries.
Again, this is not a one-size-fits-all solution. DSTs have eligibility requirements, investment risks, fees and other considerations. The episode’s larger message is about knowing that options exist and getting educated before making major real estate decisions.
Building and Transferring Generational Wealth Through Real Estate
Across all three episodes, one theme continues to emerge: real estate planning should be about more than simply selling a house.
For many families, property represents decades of work and accumulated wealth. The decisions made today can affect retirement income, taxes, family relationships and what future generations inherit.
Cory encourages families to think strategically about their real estate well before a major transition. That might mean evaluating an aging parent’s rental properties, planning a future move, determining whether a property is still performing, or beginning conversations about how real estate should eventually be transferred to children.
The series also emphasizes the importance of having the right team. Real estate decisions can intersect with taxes, estate planning, financial planning and family dynamics. No single professional can necessarily answer every question.
For seniors and adult children, the best first step may simply be to start the conversation early. You don’t have to know exactly when a move will happen. You don’t have to know whether you will eventually sell an investment property. And you don’t have to have every detail of an inheritance plan figured out. But understanding your options before you’re under pressure can give your family much more flexibility.
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Frequently Asked Questions
When should seniors start planning a move or downsizing? Ideally, before a crisis makes the decision urgent. The discussion with Cory emphasizes that downsizing can happen gradually over months or even years rather than all at once.
What is a senior move manager? A senior move manager can help coordinate aspects of a senior relocation, including organizing, decluttering, packing, moving and setting up the new home.
What is a 1031 exchange? A 1031 exchange is a tax strategy discussed in the episode that can allow qualifying investors to defer capital gains taxes when selling investment property and reinvesting in qualifying replacement property. Because the rules are complex, professional tax and legal advice is important.
What is a Delaware Statutory Trust? A Delaware Statutory Trust, or DST, is an investment structure discussed in the third episode that can allow certain investors to hold an interest in larger real estate assets without directly managing the property. DSTs can involve significant rules and risks and aren’t appropriate for everyone.
How can families protect generational wealth through real estate? Start by understanding what properties the family owns, how those properties are performing, what taxes may apply and what the family’s long-term goals are. Professional advice can help families evaluate options for managing, preserving and transferring real estate wealth.
Start Planning Before You Have To
The most important lesson from this three-part Answers for Elders series is that real estate decisions become easier when families have time to make them.
Whether you’re helping an aging parent downsize, managing rental properties, preparing for retirement or thinking about what your children will eventually inherit, don’t wait until circumstances force your hand.
Start by learning what you own, understanding its current value and performance, and having honest conversations about what you want your real estate to accomplish for you and your family.
