When should families begin planning for the later years of life? The answer may be much earlier than most people think.
For many older adults, the family home represents one of their largest financial assets. It may also represent decades of memories, independence and security. But as people age, questions about the home eventually intersect with other important decisions: What happens if the house needs to be sold? What if a parent can no longer safely live there? How will capital gains taxes affect a sale? Who will make decisions if someone becomes incapacitated? And how can parents pass assets to their children without creating confusion or conflict?
Those are some of the important questions explored in this special three-part episode of the Answers for Elders Radio Show, hosted by Suzanne Newman and featuring Certified Senior Real Estate Planner Cory Boldroff.
In the combined episode, Suzanne and Cory explore senior real estate planning, capital gains, estate planning, senior living, family communication and strategies for preserving and transferring wealth. The final segment takes an especially personal turn when Cory interviews his father, Danny Boldroff, about what he has learned about aging and planning for the future. The result is a conversation with an important message: planning ahead gives families more choices.
Senior Real Estate Planning Goes Beyond Selling a House
When an older adult considers selling a home, it’s tempting to think of the process as simply a real estate transaction. Put the house on the market, find a buyer and move on.
But senior real estate planning looks at the bigger picture.
In the first two parts of the conversation, Cory explains why homeowners need to think about the financial implications of selling property before putting it on the market. Topics include capital gains taxes, cost basis, primary residences, second homes, investment properties, capital improvements and 1031 exchanges. The key lesson isn’t that there is one magic strategy that applies to everyone. Instead, homeowners should understand their individual circumstances before making a major financial decision.
For example, the amount of appreciation in a property, how long someone has lived there, whether it is a primary residence or second home, and whether improvements have been made can all be relevant when professionals evaluate a potential sale.
The conversation also addresses inherited property and the importance of understanding how cost basis may affect a family’s financial decisions. These issues can become particularly important when adult children inherit a parent’s home and must decide whether to sell, rent or retain it. That’s why Cory encourages families to build a team of professionals rather than expecting one person to answer every question. Financial planners, tax professionals, estate planners, insurance professionals and senior real estate specialists can each bring different expertise to the table.
The broader Answers for Elders podcast library similarly emphasizes the importance of bringing different areas of senior planning together rather than treating real estate, finances, caregiving and estate planning as completely separate issues.
Estate Planning for Seniors Can Help Prevent Family Conflict
Real estate planning naturally leads to another important subject: estate planning. A will or trust isn’t simply about deciding who receives someone’s possessions after death. Thoughtful planning can also help families understand who is responsible for making decisions, who will manage assets, and what a parent actually wants.
In the third part of the episode, Cory discusses his father’s experience creating a trust and having conversations with his children about his wishes. One of the most powerful lessons is the importance of communication. Families can encounter tremendous conflict when parents die and their adult children don’t understand what was intended. Even when an estate plan is legally valid, unanswered questions can lead to suspicion, hurt feelings and disagreements.
Danny and Cory describe how their family discussed the estate plan while Danny was alive—including who would serve as successor trustee and why certain family members might receive different amounts. Those conversations weren’t necessarily easy. But they gave family members an opportunity to ask questions and understand Danny’s intentions directly from him. That is very different from siblings trying to interpret their parent’s wishes after a death.
Cory refers to this approach as a “Family Feud Prevention Plan.” The concept is simple: have difficult conversations while everyone who needs to participate is still able to participate. This philosophy is consistent with the broader Answers for Elders message that proactive estate planning can help reduce family disagreements and ensure a senior’s wishes are understood.
Aging in Place or Senior Living? Make the Decision Before You Need It
Perhaps the most personal part of the episode comes when Cory turns the interview over to his father, Danny. At 72, Danny had already experienced a long and active life. He had owned and sold three businesses, traveled extensively and remained involved with his children and grandchildren.
Like many older adults, however, he had not necessarily thought deeply about where he would want to live if he could no longer safely remain at home. Cory asked him a deceptively simple question: If you had a health crisis, where would you want to go so your family could advocate for you?
Danny’s initial answer reflected what many people might say: his wife and children would take care of him. But Cory points out that loving family members aren’t always able—or equipped—to provide every level of care a person might eventually need.
That doesn’t mean families shouldn’t help one another. It means that families benefit from discussing realistic options before an emergency occurs. Cory encouraged his father to visit senior living communities and even volunteer at one. Danny discovered something that surprised him: today’s senior living communities were very different from the institutional environments he remembered from decades earlier. He found attractive communities, private living spaces, activities, social opportunities and different levels of care. He also discovered that residents weren’t necessarily frail or isolated. Some were active and independent and were simply planning ahead for the future.
His experience illustrates an important point: you don’t have to wait until you need senior living to learn what senior living is like.
Visiting communities while you’re healthy can make a future transition less frightening—and can help families identify a preferred community before an emergency forces a rushed decision. Cory’s recommendation is particularly practical: visit, volunteer, participate in an activity and find a community where you can imagine yourself belonging.
“Blessing Your Kids While You’re Alive”
Another memorable theme from Danny and Cory’s conversation is the idea of “blessing your kids while you’re alive.” Traditionally, many families think of inheritance as something that happens after a parent dies. But Danny and Cory discuss another possibility: using thoughtful planning to help children and grandchildren during the parent’s lifetime.
In Danny’s case, that included helping family members with housing while structuring ownership and benefits through his trust. The goal wasn’t simply to give everything away. It was to find ways to help family members while Danny could still enjoy seeing the benefits of his generosity. He could visit the homes he helped his children acquire. He could see how those resources affected their lives. And he could participate in the joy of helping his family rather than only imagining what would happen after his death.
That concept adds an important emotional dimension to estate planning. Legacy isn’t necessarily just about what you leave behind. It can also be about what you get to experience with the people you love while you’re still here.
Of course, financial gifts, trusts and property transfers can have significant legal and tax implications. The episode emphasizes the importance of working with qualified professionals who can evaluate each family’s circumstances.
Build Your Family’s “Power Team” Before a Crisis
One of the most practical takeaways from this conversation is the importance of assembling a team before something goes wrong. Cory recommends that families consider having a financial planner, tax professional, insurance professional, estate planner and real estate planner working together.
Why? Because aging rarely creates just one problem. A decision to sell a house could affect taxes. A move to senior living could affect finances. An inheritance could affect multiple family members. A health crisis could require decisions about housing, care and legal authority at the same time. When professionals communicate with one another, families have a better chance of seeing the complete picture.
And planning doesn’t have to be a one-time event. Danny explains that his family revisited his estate plan as circumstances changed and consulted with his attorney over time.
That is an important reminder: an estate plan should evolve as life evolves.
Marriage, divorce, grandchildren, business sales, changing financial circumstances, health changes and changes in family relationships can all create reasons to revisit a plan.
Watch on YouTube
Part 1. Senior Homeowners – How Capital Gains Taxes Can Affect Your Home Sale
Part 2. How Seniors Can Minimize Capital Gains Taxes When Selling Real Estate
Part 3. The One Question Every Aging Parent Should Answer Now
Listen on Apple Podcasts
Frequently Asked Questions About Senior Real Estate and Estate Planning
When should seniors start planning for a future move or change in care?
Ideally, before a crisis occurs. Planning while you’re healthy gives you time to visit senior living communities, consider aging-in-place options and communicate your preferences to family members.
Do seniors automatically have to pay capital gains taxes when they sell their home?
Not necessarily. The tax consequences of a sale depend on the individual’s circumstances, including factors such as the property, its use, appreciation and cost basis. Because tax rules can be complicated, homeowners should consult a qualified tax professional before selling.
Why should parents talk to their children about their estate plan?
Open communication can help reduce confusion and potential conflict after a parent dies or becomes unable to make decisions. Danny’s experience demonstrates how discussing important decisions while everyone is together can give family members an opportunity to understand the parent’s wishes.
Is a living trust the same thing as a will?
No. Trusts and wills serve different purposes and have different legal implications. The appropriate estate-planning documents depend on an individual’s circumstances and state law, so families should work with a qualified estate-planning attorney.
What is the biggest lesson from this episode?
Don’t wait for a crisis. Whether you’re thinking about selling a home, planning for senior living, protecting assets or creating an estate plan, starting the conversation early gives you and your family more time—and more choices.
Planning Today Can Give Your Family Peace of Mind Tomorrow
Aging is unpredictable. No one knows exactly when a health crisis might occur, how long someone will be able to remain in their home, or what financial and family circumstances may look like years from now.
But families don’t have to know exactly what will happen in order to prepare:
- They can talk about possibilities.
- They can visit senior living communities.
- They can review their estate documents.
- They can understand the financial implications of selling property.
- They can communicate their wishes.
- And they can build a team of trusted professionals before they urgently need one.
That may be the most important message from Suzanne Newman, Cory Boldroff and Danny Boldroff’s conversation: good planning isn’t about expecting something bad to happen. It’s about giving yourself and the people you love the freedom to make better decisions when life changes.
This article is for educational purposes and reflects the discussion in the Answers for Elders episode. Tax, legal, financial, insurance and estate-planning decisions are highly individual. Consult appropriately qualified professionals for advice about your specific circumstances.
