Moving to Senior Living? Done Being a Landlord? Protect Real Estate Wealth

Moving after decades in the same home can be one of the most stressful transitions in later life. In Part 1 of this three-part Answers for Elders conversation, host Suzanne Newman sits down with Cory Boldroff, a certified senior real estate planner, to discuss how older adults and their families can make the moving and downsizing process easier, more organized, and less overwhelming. Cory explains why senior moves are different and how specialized professionals can help families navigate decluttering, packing, moving, setting up a new home, and the emotional challenges that often come with leaving a longtime residence.

For seniors considering a move to senior living—or adult children helping an aging parent—planning ahead can make a tremendous difference. Cory shares the role of a senior move manager, including how these professionals can coordinate the move, create a plan for furniture and belongings, and even help arrange a new home before the senior arrives. The conversation also explores strategies such as moving before a crisis occurs, using respite or guest accommodations while a new residence is prepared, and taking a methodical approach to downsizing rather than trying to do everything at once.

The discussion also covers estate sales, donations, junk removal, and other resources that can help families deal with years of accumulated belongings without taking on unnecessary stress. Cory emphasizes that families don't have to handle every part of a senior move themselves. He encourages older adults to begin planning years before a move becomes necessary. If you or a parent are thinking about downsizing, aging in place, moving to senior living, or selling a longtime family home, this episode offers practical senior moving tips and strategies for making the transition smoother.

What should you do with an investment property that has appreciated significantly—and how can you potentially preserve more of the wealth you've built? Cory talks about investment property strategies, real estate taxes, capital gains, depreciation, and the importance of regularly evaluating whether a property is still performing well. Cory explains why simply collecting rental income doesn't necessarily mean an investment property is a good investment and discusses factors such as cash flow, cap rate, return on investment, taxes, insurance, maintenance and leverage.

A major focus of this episode is the 1031 exchange, a strategy that can allow an investor to defer capital gains taxes when selling one investment property and reinvesting in other qualifying investment properties. Cory explains some of the important timing and process requirements, including identifying replacement properties within 45 days and completing the purchase within 180 days. He also emphasizes that these transactions require careful planning and the right professionals because mistakes can result in unexpected tax liability.

Cory also shares a real-world example of repositioning an under-performing property into multiple replacement properties, as well as his broader philosophy of using real estate as a tool for wealth accumulation and generational wealth preservation. The conversation touches on the concept of a stepped-up cost basis at inheritance, evaluating real estate during changing market conditions, and working with a qualified real estate and tax-planning team before making major decisions.

What happens when older adults own investment properties but no longer want the responsibilities of being a landlord? Cory explores Delaware Statutory Trusts (DSTs). They talk about how the trusts may provide an alternative for certain investors who want to move out of active real estate management while continuing to participate in real estate. Cory explains how DSTs can be used in connection with a 1031 exchange and discusses why they may be worth considering for seniors who have accumulated significant real estate wealth but are tired of managing rental properties, dealing with repairs, or handling tenants.

The conversation takes a closer look at how a DST works. Cory describes a structure in which investors can purchase an interest in larger commercial properties, potentially including institutional or “blue chip” properties, without becoming the day-to-day landlord or property manager. The episode discusses potential income, the hands-off nature of the arrangement, how DST interests can fit into a 1031 exchange strategy, and how ownership interests may provide flexibility when planning for an inheritance. Cory also explains how a DST could potentially help families think about wealth transfer when different heirs have different financial goals.

For seniors and families thinking about real estate wealth, capital gains taxes, retirement planning and generational wealth, this episode highlights the importance of understanding your options before selling an investment property. Cory emphasizes education and working with qualified professionals to evaluate strategies such as 1031 exchanges and DSTs, particularly because tax consequences and eligibility requirements can be significant. The discussion also looks at how real estate planning can help families think beyond simply selling property—toward protecting, transferring and potentially continuing to build the wealth they've accumulated over their lifetimes.

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