As we get older, some of the most important financial and lifestyle decisions we make are connected to one another. Your home may be your largest asset. Insurance may play an important role in protecting your family and your legacy. And eventually, you may need to think about how you will pay for care—whether you remain at home, hire home care, or move into a senior living community.
Those decisions can be difficult to navigate, especially when families wait until a health crisis forces them to act. Suzanne Newman sits down with Cory Boldroff, a certified senior real estate planner and head of the senior planning division at Axon Realty, for a three-part conversation about building, protecting and preserving wealth while preparing for the realities of aging.
The conversation covers real estate wealth strategies, life and homeowners insurance, long-term care planning, aging in place, senior living, Medicaid considerations, home equity and reverse mortgages. While these subjects can seem separate, Cory’s message throughout the conversation is that families benefit from looking at them as pieces of one larger plan.
Real Estate and Building Wealth for the Future
For many older adults, the family home represents much more than a place to live. It may be one of the largest assets they own—and potentially an important part of their family’s financial legacy. Cory explains that real estate can create wealth in several different ways. These include appreciation, leverage, potential cash flow, tax advantages and diversification. For families who own multiple properties or have substantial equity in their home, understanding how those assets fit into an overall financial plan can become particularly important as retirement approaches.
The conversation also explores what happens when parents want to leave real estate to their children. Decisions about ownership, trusts, inheritance and the timing of transferring assets can have significant financial implications. That is why Cory encourages families to think about these questions before a crisis occurs. Instead of simply asking, “What happens to my house when I’m gone?” families can begin asking broader questions:
- Is my home still the right home for me?
- How does my real estate fit into my retirement plan?
- What do I want to leave to my children?
- Should I consider using some of my home equity?
- How might my real estate help me pay for future care?
There isn’t one answer that works for every family. The important first step is understanding what options exist.
Life Insurance and Protecting Generational Wealth
The second part of the conversation turns to insurance—and particularly the role life insurance may play in protecting family wealth.
Cory discusses strategies sometimes referred to as the “Rockefeller” or “waterfall” approach, in which life insurance and trusts can be structured as part of a broader generational wealth strategy. He also explains different types of life insurance and why families should understand how their existing policies actually work. For some people, life insurance is simply about replacing income or providing financial protection for loved ones. For others, it may become part of a larger estate or legacy strategy.
The conversation also touches on life insurance settlements. In certain circumstances, someone who owns a policy they can no longer afford may have the option of selling the policy rather than simply allowing it to lapse. Cory also discusses policies that may include long-term care riders or other living benefits.
These are complex financial decisions, and the right choice depends on an individual’s circumstances, policy terms and applicable laws. But the larger lesson is straightforward: don’t assume an insurance policy is simply something you pay for and forget about. It can be worth periodically reviewing what coverage you have, what it costs, what benefits it provides and how it fits into your larger financial and estate plan.
The discussion also expands to homeowners insurance and the challenges families are facing as insurance costs and availability change in some parts of the country.
Long-Term Care Planning: Don’t Wait for a Crisis
Perhaps the most important part of the conversation for many families is the discussion about long-term care planning. People often don’t want to think about the possibility that they might eventually need help with everyday activities. Many hope they will remain completely independent and continue living at home indefinitely. And that may happen. But planning for another possibility doesn’t mean giving up on independence. In fact, planning ahead can help make aging in place more achievable.
Cory talks about practical changes that can make a home safer as someone gets older. These include installing grab bars near toilets and showers, eliminating dangerous step-overs, addressing stairs and changes in floor level, improving nighttime lighting and eliminating trip hazards. These may seem like small modifications, but they can become very important when mobility or balance changes.
Cory also encourages families to think beyond the physical house. What happens if someone eventually needs help with meals, bathing, transportation or medications? Who will coordinate that care? What home care agencies are available? What senior living communities are nearby? These questions are much easier to explore while everyone is healthy than during an emergency.
Understanding Senior Living Before You Need It
One particularly useful point from the conversation is Cory’s recommendation that families visit senior living communities before they need one. A visit isn’t a commitment to move. Instead, it gives older adults and their families an opportunity to understand what is available, compare different communities, learn about costs and discover the differences in services, culture and levels of care.
Cory also encourages people to think differently about what they are purchasing when they move into senior living. Rather than looking only at the size of an individual apartment, consider the larger lifestyle and support system available around it—including dining, activities, fitness, social opportunities and assistance with household responsibilities.
For someone who has spent decades maintaining a home, the value may be about more than square footage.
Medicare, Medicaid, Home Equity and Your Long-Term Care Plan
Paying for long-term care is another issue families need to consider well in advance. The conversation discusses Medicare and Medicaid, including the importance of understanding eligibility rules and the potential consequences of transferring assets. Cory specifically cautions families against simply giving a home or other property to children without first understanding the financial and eligibility implications. Medicaid rules can be complicated and vary by state, so families should seek advice from qualified professionals who understand their specific circumstances.
The conversation also looks at home equity and reverse mortgages as potential tools for some older adults who want to remain in their homes. A reverse mortgage isn’t right for everyone, but Cory explains why it can be worth understanding rather than automatically dismissing.
The key isn’t choosing a particular financial product. It’s creating a plan that considers your home, your resources, your desired lifestyle and the kind of care you may eventually need.
The Most Important Step: Start Planning Before You Need To
One of the strongest themes here is the value of planning before a crisis. Your financial plan shouldn’t exist separately from your aging plan. Your home, insurance, estate plan and potential long-term care needs can all affect one another.
For older adults, that might mean taking a fresh look at whether the current home will work for the next 10 or 20 years. For adult children, it might mean having a conversation with Mom or Dad before a hospitalization or sudden health change makes the conversation urgent. And for families of any age, it can mean learning what resources are available before they’re needed.
The goal isn’t to predict exactly what will happen. It’s to create enough knowledge and preparation that you have choices when circumstances change. The best time to start planning for long-term care, aging in place and protecting your family’s assets is before you need to make those decisions under pressure.
Watch on YouTube
Part 1. How Seniors Can Build and Transfer Wealth Through Real Estate
Part 2. How Life Insurance Can Protect Generational Wealth
Part 3. Long Term Care Planning: How to Prepare for Aging at Home
Listen to the Full Apple Podcasts Episode
Frequently Asked Questions
What is long-term care planning?
Long-term care planning involves thinking ahead about where and how you might receive assistance if you eventually need help with everyday activities. It can include planning for aging in place, home care, assisted living or other senior living options, as well as considering how care may be paid for.
Should I plan for long-term care even if I want to age in place?
Yes. Planning for long-term care doesn’t mean you have to leave your home. In fact, understanding potential home modifications, home care services, costs and available resources can help you prepare to remain safely at home for as long as possible.
How does my home fit into my long-term care plan?
Your home may be your largest financial asset, but it is also the place where you may want to remain as you age. Families may need to consider home modifications, ongoing maintenance, home care costs, downsizing, selling, using home equity or other options. The appropriate strategy depends on your individual circumstances.
Should families visit senior living communities before they need one?
Visiting in advance can be extremely helpful. It allows older adults and their families to compare communities, understand available services and get a realistic sense of costs and lifestyle without having to make a decision during a crisis.
Can life insurance be part of an estate or long-term care plan?
It can be, depending on the policy and the individual’s circumstances. Life insurance may provide financial protection, and some policies may offer living benefits or long-term care-related provisions. Families should review specific policies with appropriately qualified financial and insurance professionals.









