Into the Woods

Episode 28 – Medicaid Applications: The Documentation Gauntlet

In this episode, Dave Shaffer, Hannah Mills, and Kristel Martini discuss the documentation process for Medicaid applications, covering deadlines, caseworker requests, and tips for navigating the five-year lookback requirement.

Episode 27 – Will Contests: When Family Fights Back

In this episode, Dave Shaffer and Hannah Cannon discuss the legal grounds for contesting a will in New York, no-contest clauses, and lessons from the movie Knives Out about why will challenges rarely succeed.

Episode 26 – Digital Legacy Planning: Beyond the Will (Part 2)

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.

Episode 25 – Electronic Wills: Welcome to the Digital Age (Part 1)

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.

Episode 24 – Transfer on Death Deeds: Does New Mean Good?

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.