Into the Woods

In Part 2 of their digital estate planning series, Dave Shaffer and Caroline Cercone discuss digital legacy planning, explaining why you need both a legal will and a social media plan—plus a Taylor Swift-themed breakdown of how each works.

In Part 1 of their electronic wills series, Dave Shaffer and Caroline Cercone discuss New York's new digital will law (effective December 2027), covering how it works, the risks involved, and lessons from the Samsung Galaxy Will case.

In this episode, Dave Shaffer and Morgan Napierski discuss New York's new Transfer on Death deed law, explaining the limitations and pitfalls that make this probate avoidance tool less useful than it seems for most families.

In this episode of Into the Woods, attorney Hannah Mills joins host Dave Shaffer to explain why estate planning isn’t just for older generations. They cover New York’s intestacy laws, planning considerations for young families, unmarried couples, and business owners, and share a cautionary tale about the author of The Girl with the Dragon Tattoo.

In this episode of Into the Woods, host Dave Shaffer and estates paralegal Deana Kilpatrick walk through the 10 immediate steps families should take when a loved one passes away – from obtaining death certificates and finding the will to tracking assets, managing debts, and knowing when to seek legal guidance.

In Part 2 of their teamwork series, Dave Shaffer and Hannah Cannon discuss estate administration, tax filing requirements, and the importance of working with financial advisors—plus a $21 million lesson about fiduciary duty.

In Part 1 of their teamwork series, Dave Shaffer and Hannah Cannon discuss why estate planning requires collaboration between lawyers, financial advisors, and insurance agents—plus a cautionary case about the cost of failing to coordinate.

In Part 2 of their real estate series, Dave Shaffer and Tom Rickettson discuss trusts and LLCs as tools for avoiding probate, protecting assets, and managing property—plus celebrity examples of creative trust naming for privacy.

In this special video episode filmed at the WOG holiday party, Dave Shaffer and Caroline Cercone preview the top 5 estate planning trends for 2026—including New York estate tax strategies, gifting, asset protection, and digital asset planning.

In Part 1 of their real estate series, Dave Shaffer and Tom Rickettson discuss how property ownership affects estate planning, explain common deed structures, and share lessons from HBO's Succession about the importance of planning ahead.

In this episode, Dave Shaffer and Caroline Cercone discuss the fundamentals of charitable giving, including donor-advised funds, private foundations, and charitable trusts. They share practical planning advice and a cautionary tale about vetting charities before you donate.

In Part 2 of their series on the five-year Medicaid lookback period, attorneys Dave Shaffer and Hannah Mills discuss overlooked transactions that can count as gifts, share lessons from a real fair-hearing case, and offer documentation tips to help families avoid costly Medicaid penalties.

In this episode, attorneys Dave Shaffer and Hannah Mills explore the five-year Medicaid lookback period, explaining how it works, why it matters, and sharing a real fair hearing case about the consequences of making gifts to family members—even with good intentions.

In this episode, attorneys Dave Shaffer and Hannah Cannon explore the critical role of beneficiary designations in estate planning, explaining how these often-overlooked forms can override your will and sharing lessons from a Supreme Court case about the costly consequences of neglecting to update them.

In this episode, attorneys Dave Shaffer, Kelly Gusmano, and Hannah Mills explore asset protection trusts for Medicaid planning, explaining how these irrevocable trusts can protect your home and investments from nursing home costs while preserving your right to live comfortably.

In this episode, attorneys Dave Shaffer and Morgan Napierski explore the fundamentals of trust planning, explaining when trusts are necessary, how they work, and the critical importance of proper trust funding.

In this episode, attorneys Dave Shaffer and Caroline Cercone explore the probate process, debunking common misconceptions while explaining when to avoid probate and when court oversight can actually protect your loved ones.

In this episode, attorneys Dave Shaffer and Hannah Cannon explore the nuances of supplemental needs trusts—choosing the right trustee, lifetime gifting options, and planning ahead for both loved ones and individuals with disabilities.

In this episode, attorney Hannah Cannon joins host Dave Shaffer to explain supplemental needs trusts—what they are, why they matter, and how they protect government benefits for loved ones with disabilities.

In this episode, Hannah Cannon joins Dave Shaffer to break down the ins and outs of gifting—what’s allowed, what’s reportable, and how it fits into estate and Medicaid planning.    Disclaimer: Episode recorded before passage of the One Big Beautiful Bill Act and the extension of the current federal estate tax exemption to $15M in 2026.   

In this episode, Morgan Napierski joins host Dave Shaffer to explain the crucial roles of executor and power of attorney—what they do, how they differ, and why naming the right person can protect your legacy and your loved ones.

In this episode of Into the Woods, attorney Kelly Gusmano joins host Dave Shaffer to discuss how Community Medicaid can help cover the costs of in-home care. They explore eligibility requirements, explain how family members can be paid as caregivers through the CDPAP program, and discuss strategies for qualifying while preserving assets—particularly in light of potential rule changes coming in 2026.

In this episode of Into the Woods, attorney Christen Bruu joins host Dave Shaffer to discuss planning strategies for family vacation properties. They explore the risks of leaving cottages to multiple heirs without structure, compare the benefits of LLCs versus trusts for property management, and share practical advice for preserving these treasured family assets for generations to come.

In this episode of Into the Woods, attorney Hannah Cannon joins host Dave Shaffer to discuss estate planning considerations for New Yorkers who spend winters in Florida. They cover essential legal documents for both states, strategies to handle Florida real estate, and explain how the Florida homestead exemption works for those considering a permanent move south.

In this episode of Into the Woods, attorney Morgan Napierski joins host Dave Shaffer to discuss why having a will matters. They cover New York’s intestacy laws, the role of executors, and how to ensure your assets are distributed according to your wishes.

In this episode of Into the Woods, elder law attorneys Rick Marchese and Kelly Gusmano join host Dave Schaffer to discuss the complexities of nursing home admission agreements. They cover financial applications, key contract provisions, and how families can protect themselves while ensuring quality care for their loved ones.

In this episode of Into the Woods, elder law attorneys Rick Marchese and Kelly Gusmano join host Dave Shaffer in guiding you through the complexities of long-term care, Medicaid, and protecting your family’s finances. With expert advice and real-life examples, they break down key decisions and offer practical solutions for families facing elder care challenges.