It’s not about passing down real estate . . .
It’s about preserving the property and the relationships attached to it.
Vacation Home Planning Guide helps families think through the practical questions that determine whether a shared property can be preserved successfully.
Whether your family is beginning the conversation, preparing to meet with an attorney, or trying to bring structure to an informal agreement, this book will help you plan it, share it, and keep it.
Vacation Home Planning Guide
Plan It. Share It. Keep It.
Behind every “camp,” “beach house,” or “lake house” there’s a history — part money, part memory. And the longer a family owns a vacation home, the more complex managing it becomes. Parents want fairness. Children want clarity. Everyone wants peace.
The Challenge: How to preserve a beloved family vacation home without destroying the relationships that made it worth keeping in the first place?
This book shows you how to get there.
The book includes access to a full set of downloadable printable worksheets for your own use, or to share with your co-planners.
These notes and worksheets will provide your attorney with a working draft of your agreement.
Between the Covers
Stories that Resonate
You may find yourself inside one of the stories . . . these are fictional but based on the real issues families face. Each chapter begins with a relatable story, outlining how the friction inherent in sharing a vacation home can wear on the property and the family ties. Each chapter takes the lesson and explains the methods used to avoid conflict and restore peace.
Guided Exercises
After the story and discussion of the chapter’s main decision point, there is a focussed worksheet to guide you through your own evaluation of your property and family goals and how to apply strategies to mitigate conflict and maximize successful planning.
The book includes access to a full set of downloadable printable worksheets for your own use, or to share with your co-planners.
These notes and worksheets will provide your attorney with a working draft of your agreement.
Information
The Explainers chapter takes you through a deeper look at the concepts, showing how one choice versus another will play out over time. This chapter is written in plain language. A glossary of the terms used throughout the book is also included.
Full Sample Agreement
The final chapter presents a fictional family, and the circumstances they are working through in creating an agreement that will shield both their relationships and their property for themselves and their heirs.
The resulting agreement is presented, with references from and to the fictional family saga, to help you see how plain language goals are translated into “legalese” to help demystify the process.
The Trail of Decisions
Planning to keep a vacation home for generations isn’t one decision. It’s a process and a path through major decision milestones.
Vacation Home Planning Guide helps you navigate the path.
The First Decision
Consider the options of whether to take your vacation home into your family’s future or liquidate the asset and distribute it among them.
What Counts for Membership?
Determine who is family . . . whether it is blood or something else that counts for inclusion in membership responsibilities and priveleges.
Sharing and Enjoying the Property for Generations
How will your family share the property, especially as the family grows? Learn about the strategies successfully used to determine what is fair when sharing a vacation property, and how to enforce the family rulebook while keeping disagreements out of court.
Fairly Assessing and Managing the Finances
Learn the strategies for successful management of the upkeep of the property. From taxes to maintenance and improvements, how to share the burden without breaking the peace.
Insulating the Property from External Threats
Strategies most common for protecting the property from vulnerabilities – like tax liens or lawsuits.
More to Know if You Need It
A full chapter of plain language explainers on how legal frameworks like branching, governance, trusts, and LLCs work to support the family goals for the property.
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Want the full conversation?
Every family thinks their vacation home will last forever — but most don’t make it past the next generation. Not because families don’t care—but because no one planned for what comes next.
In this episode of LifeCast, Attorney Jesse Bifulco sheds light on why a family vacation property rarely makes it past the second generation, and the difference between inheritance by default and legacy by design.
Watch more LifeCounsel videos on YouTube.
LifeCounsel exists to educate, inform, and inspire — so you can make better decisions for your family and your future.
I’m Jesse Bifulco, a practicing attorney who once imagined the lawyer’s role as battling it out in the courtroom. Over time, I came to realize that what most families need is not a litigator — it’s a counselor. Not someone who wins arguments after they begin, but someone who helps prevent them in the first place.
That realization led me to focus exclusively on estate planning.
After helping thousands of families protect what truly matters — not only their assets, but their stories, relationships, and peace of mind — I’ve come to see estate planning differently. It is not simply planning for what happens after life. It is planning for life itself.
Information provided for educational purposes only and does not constitute legal or investment advice, or create an attorney-client relationship.
For personalized guidance, please consult a licensed attorney or financial advisor.