Life, Legacy & Wealth

In this episode of Life, Legacy & Wealth, Cary Moss breaks down everything families need to know about Medicaid planning — before a crisis forces their hand. From the five-year lookback rule to irrevocable trusts, spousal refusal, and the caregiver child exception, Cary walks through the legal strategies available to Florida families who want to protect their assets and preserve their legacy without running afoul of Medicaid rules. Cary brings years of hands-on elder law experience to the conversation, offering practical guidance on what documents to gather, what questions to ask when hiring an elder law attorney, and what steps families can take right now — even if a nursing home is still years away. If there’s one thing to take away from this episode, it’s this: don’t wait for a crisis to start planning. In this episode, you will hear: The five-year lookback rule and why timing is everything…

In this episode, Cary Moss breaks down one of the most misunderstood rules in Florida elder law — the five-year Medicaid lookback period. Families are constantly caught off guard by this rule, making costly mistakes like transferring assets to children or adding names to property deeds, only to discover these moves can trigger serious penalties when it comes time to apply for Medicaid. Cary walks through how penalty periods are calculated, which transfers are exempt, and how tools like personal care contracts can protect a family’s assets while staying fully compliant. She also tackles tricky real-world scenarios — from grandparents paying college tuition to families compensating a child for in-home caregiving — and explains how proper documentation can mean the difference between approval and denial. Don’t let a lack of planning cost your family everything — this episode could save you thousands. In this episode, you will hear: Why transferring…

Choosing the right trustee is one of the most important — and most overlooked — decisions in estate planning. In this episode, attorney Tom Moss breaks down what families need to know before naming a trustee, from red flags that signal the wrong choice to the “desired behaviors” clauses that can reduce family conflict before it starts. Tom also tackles the co-trustee question, the case for corporate trustees, and why “keeping things equal” isn’t always the right approach. Whether a trust is already in place or just getting started, this episode offers a practical roadmap for making one of the most consequential decisions a family will face. In this episode, you will hear: Why “keeping things equal” can actually breach the peace Red flags that disqualify a trustee before they even start How “desired behaviors” clauses give trustees clear guidance When co-trustees are a blessing — and when they’re a…

Choosing the right trustee can protect a family’s legacy—or create years of conflict. In this episode, Tom Moss breaks down what trustee selection really means and why it goes far beyond picking the child who is “good with money.” He explains the true definition of a fiduciary, the legal duties involved in trust administration, and the emotional weight placed on someone asked to manage assets for siblings or loved ones. Tom walks through the practical differences between trustees and personal representatives, common family conflict triggers, co-trustee pitfalls, corporate trustee pros and cons, and Florida-specific considerations like annual accountings and U.S. citizenship requirements. If an estate plan is meant to preserve both wealth and relationships, this conversation offers a clear roadmap for doing both well. In this episode, you will hear: What a fiduciary really is and the legal duties of a trustee Trustee vs personal representative and why court oversight…

In today’s episode of Life, Legacy & Wealth, we continue the conversation around Medicaid planning, nursing home costs, and asset protection—and the costly mistakes families often make when they try to navigate this process on their own. I’m joined again by elder law attorney Cary Moss, who shares real-world examples from her practice that show how well-intended decisions can create serious financial and legal problems if they’re not done correctly. Cary breaks down common red flags, including gifting assets, adding children to accounts, misunderstanding special needs trusts, and relying on incorrect advice from friends or the internet. We also walk through a powerful success story that shows how proper planning can protect a spouse, preserve assets, and bring peace of mind during an incredibly stressful time. If you or your family are thinking about long-term care, Medicaid eligibility, or protecting what you’ve worked so hard to build, this is a…