The Death Readiness Podcast

Episode: 47

Title: How to Stop the Family Camp from Splitting Siblings

Host: Jill Mastroianni (Solo)

Published: November 25, 2025

Jill Mastroianni (00:00): Does your family have a special place where you’ve built a lifetime of memories? Maybe it’s the house you grew up in. Maybe it’s a grandparent’s cottage, or a lake house that has quietly held your family’s traditions for decades. And maybe, just maybe, someone in your family has said, “We want this place to stay in the family forever.”

But what does that actually mean? Do the next generations understand the emotional and financial weight of that promise? And even more importantly… is it what they really want?

Welcome to the Death Readiness Podcast. This is not your dad’s estate planning podcast. I’m Jill Mastroianni, former estate attorney, current realist, and your guide to wills, trusts, probate and the conversations no one wants to have. If your Google search history includes, “Do I need a trust?” “What exactly is probate?” and “Am I supposed to do something with mom’s Will?” you’re in the right place.

(01:15) As we head into Thanksgiving, I’ve been thinking a lot about gratitude. And recently, something happened that reminded me how lucky I am to do this work.

I just returned on Saturday afternoon from a trip to Nashville. A podcast listener named Becky lives in the same neighborhood as my law school roommate, Alex, who has a very on-brand yard sign advertising The Death Readiness Podcast on her front lawn. Becky saw the sign, started listening, reached out, and before I knew it we were messaging, hopping on Zoom, and she was inviting me to speak to a couple of professional groups in Nashville. She even hosted this beautiful and delicious dinner, all, I’m sure, while juggling about a thousand personal and professional obligations.

I’m so grateful for Becky, for reaching out, for being generous, and for the thoughtful way she made space for me in her world.

And it made me think about something else I’ve always been grateful for, the Adirondack Mountains, and the tiny lake where my dad still lives.

(02:23) Growing up, that house wasn’t just a house. It was the place where I watched my parents and their friends Hal and Pam take dilapidated old Higby Club buildings, relics of a long-gone lakeside resort that had its heyday in the early to mid-1900s, and turn them into homes, or, camps, as they’re called up there. It was where I consulted Pam, who I thought was the smartest person alive, on my sixth-grade egg drop project. That’s where Hal performed the marriage ceremony for me and my husband on a shared dock. It’s where my daughter has grown from a little kid into a full teenager over consecutive summers.

And there’s this wallpaper border in the downstairs bathroom of my dad’s home, a border I helped my mom put up. Behind it, hidden, is our failed attempt at sponge-painting hydrangeas. My mom said, “Someday, after I’m gone, you’ll take this border down and see those hydrangeas.”

(03:27) I haven’t taken it down. Neither has my dad. I know exactly where they are. And even though my mom has been gone 13 years, even though she died in that house, in the bedroom just up the stairs, it still feels like a little piece of her lives behind that wallpaper.

And here’s the thing I keep coming back to:

I get to take those memories with me. They don’t live in the deed to the property. They live in me.

Maybe I’ll never uncover that hydrangea. Maybe a future owner will. But the memory of creating it, that’s mine, whether or not I ever inherit that house someday.

During this recent trip to Nashville, I stayed with Hal and Pam’s son Jeremy. He welcomed me, and my dog Hopper, into his home. Something else to be grateful for.

(04:23) Before I headed out of town, Jeremy and I took Hopper for one last loop around the neighborhood. We talked about our futures, and I told him that I’ve been so consistently wrong about predicting my own that I’ve finally stopped guessing. I said, “Who knows… maybe we’ll both find ourselves back at the lake someday.”

The lake is a possibility, not an expectation. It’s not something either Jeremy or I are owed. It’s simply one of many futures we might build for ourselves, a future in which we’re the ones responsible for creating joy and meaning and memories, wherever we happen to land.

Every time someone brings up “the family home” or “the camp” or “the cottage,” it starts the same way:“You will not believe the story of what happened in my friend’s family…”

And almost always, the drama centers around the most emotionally loaded, and logistically complicated, asset families ever try to pass down: real estate.

(05:27) So today, we’re going to talk about why it gets so messy. On this Tuesday Triage, I’m not answering a question from one specific listener, I’m answering a collective plea I’ve heard over and over: 

How do we keep this from becoming a disaster?

The truth is, we talk about it. We remove the guesswork. We figure out who actually wants to be involved, who can realistically afford to participate, and we allow the owner, the person with the legal power to decide, to make choices with eyes wide open. Ideally, those choices are aligned with the next generation as much as possible, but rooted in reality instead of assumptions.

I’ve included my Family Discovery Worksheet in the show notes. It will guide you into these conversations gently, without putting anyone on the spot.

(06:21) And I’m going to walk you through five key discussion topics, starting with:

#1: Focus on the math, not the memories.

Families romanticize the place. The dock. The sunsets. The mugs that don’t match.

What they don’t romanticize is the actual cost of keeping the camp, the lake house, the family vacation property. And those costs are not small. Or predictable. Or one-time expenses.

I’m talking about things that show up every single year, whether anyone visits the place or not. These expenses include, but are definitely not limited to, property taxes, insurance, HOA fees, lawncare, snow plowing and watercraft storage.

Most would-be beneficiaries have no idea what it actually costs to keep a property like this running, not just for one season, but for decades. And why would they? They’ve only ever seen the place as kids or as guests. They arrive when the beds are made, the water’s turned on, and the dock is magically in the water.

(07:29) They don’t see the behind-the-scenes work that keeps the place running: the generator maintenance, the broken water pump in July, or the roof leak that shows up in the dead of winter.

And it’s worth saying plainly:

Sentiment does not pay the fuel truck.

Love for the lake does not replace a roof.

And nostalgia will not stop the dock from collapsing.

The math is the math, regardless of how magical the memories are.

A family property isn’t just something you inherit; it’s something you fund. 

And until everyone sees the numbers in black and white, decisions get made based on emotion instead of reality.

#2: Do not assume everyone sees “fairness” the same way.

(08:17) Fairness is a kind of perspective, and everyone will see it a bit differently.

Some think fairness means:

• Split everything equally.

• Everyone gets equal time in July.

• Every sibling contributes the same amount.

• No rentals. Ever. The camp is for family only.

Others think fairness means:

• Whoever uses it most should pay more.

• Whoever pays more should get more control.

• Renting is necessary to cover costs.

• No one should be forced into owning something they can’t afford.

Neither of these perspectives is wrong. They each come from different lived experiences and different priorities.

Unfortunately, these unspoken different perspectives is where families get into trouble: Everyone quietly assumes that their version of “fair” is the obvious one. And no one realizes how wildly misaligned the expectations are until the owner dies — and suddenly everyone is offended.

(09:21) One sibling thinks everyone should pitch in. Another thinks pitching in only counts if it’s financial. Another thinks they shouldn’t have to pay if they barely use the property. Another thinks use shouldn’t dictate payment at all.

Without intentional conversations, every sibling believes they are being reasonable… and that someone else is being selfish.

This isn’t a character flaw. It’s a communication flaw, and one that is largely preventable.

#3: Remember that the camp is a financial asset.

Recognizing that the camp is a financial asset makes people uncomfortable because it feels like we’re assigning dollar signs to emotional history. But the financial reality matters, because ignoring it is exactly how families end up fractured.

A family property isn’t just the backdrop to decades of memories. 

It’s an asset with a market value and carrying costs.

(10:23) And here’s where families get into trouble:

The person who loves the camp the most is often the person who can least afford it.

They’re the one who:

• Spends the most time there

• Feels the most sentimental attachment

• Promises, “I’ll figure it out”

• Doesn’t want to sell because it feels like losing a piece of their identity

So what happens?

They inherit it. They try to keep it afloat. The taxes, maintenance, and unexpected repairs start to pile up. They take on debt. They feel ashamed asking siblings for money. And eventually… they sell it, fast.

Not because they didn’t care but because they cared so much they backed themselves into an unsustainable corner.

And then the siblings who didn’t inherit it? They’re heartbroken. They’re angry. They feel like something sacred was taken from them.

What kind of legacy does an unstructured and unspoken plan leave behind?

(11:24) Parents often picture the camp as the place that will keep the family together, the gathering point for future generations.

But when parents say, “My kids will figure it out,” without a plan, without structure, without a real discussion about money, capacity, and fairness, the “legacy” can go very differently:

Not shared memories. Not family reunions. Not cousins piling into bunk beds.

But siblings who no longer speak to each other.

Parents never intend that outcome. But that’s the risk when the financial reality is ignored and the burden of decision-making is dumped on the next generation.

You can’t pass down a property and expect your kids to magically agree on something you never took the time to plan or help them understand.

A camp is not a neutral inheritance. It’s a responsibility, one that requires clarity, planning, and honest conversations while the owner is still living and capable of making decisions.

#4: Your parent’s property is NOT your property.

(12:34) We do not have forced heirship in the United States.

You are not entitled to your parents’ camp. You are not guaranteed an ownership interest. Your parents, and only your parents, get to choose what happens to their property, not you.

They can:

• Sell the property

• Leave it to one child

• Leave it to none of the children

• Leave it to a grandchild

• Leave it to the neighbor down the road

• Donate it to a land conservancy

You may not like the decision. You may not agree with it or understand it. But you are not legally entitled to anything. The decision rests with your parents.

And this is where gratitude, especially in anticipation of Thanksgiving, is helpful.

(13:25) My parents gave me something bigger than the house. They gave me the time I’ve already spent there, the dockside celebrations, the almost too-dangerous sledding, the summer nights at the bonfire, lakeside basketball games on a makeshift court, the holiday champagne chilling in the snow, and the morning stillness that steadies me now, just as much as it did when I was an angsty teenager.

All of that is mine forever, and none of it requires inheriting the deed.

The gift was the experience, not the asset.

#5: You can choose to build new memories.

This is the part people forget:

If you never inherit the camp… if your sibling does inherit it… if the property gets sold…if the owner makes a decision you weren’t expecting, you don’t lose the memories.

And you gain something meaningful: the freedom to create your own version of the camp, without the financial or emotional strain.

(14:30) And instead of funneling your emotional energy into resentment or disappointment, you get to redirect it into building something new:

• A different lake

• A rental cabin

• A long weekend with your kids

• A family reunion somewhere new

• A backyard tradition that becomes the next generation’s nostalgia

• A hiking trip, a beach trip, a holiday getaway

You get to create your own place of meaning. Your own anchor. Your own version of what the camp represented.

Because the memories were never in the deed. They were never in the square footage. They were never tied to that one specific building.

The memories were in the people who gathered there. And you get to carry those memories with you, wherever you go.

So… what do families need to do to avoid turning a beloved place into the source of family warfare?

(15:26) I’ve distilled the answer into four key steps. And all four require something families are notoriously bad at: talking before there’s a crisis.

Step 1: Have the conversation now.

Not after someone dies and everyone is grieving, exhausted and already on edge. Not after someone takes charge by default.

I’m talking now, while the owner is able to say out loud what they want, what they don’t want, and what they’re actually expecting from their children or beneficiaries.

Use the Family Discovery Worksheet that I’ll link to in the show notes to spark these conversations:

• What does the property actually mean to each person?

• Does everyone truly want to keep it, or is someone afraid to say no?

• What are each person’s hopes? What are their fears?

• What does “stay-in-the-family” even mean?

• How much work and money is each person willing, and able, to contribute?

(16:27) These questions bring the unspoken tensions into the open, where they can be addressed before they blow up into lifelong resentments.

If you don’t talk about expectations, people will create their own, and that’s where conflicts begin.

Step 2: Get real about the costs

This isn’t about scaring anyone; it’s about telling the truth. 

The camp costs what it costs. The maintenance takes what it takes.

Everyone needs to see the full financial expenses in black and white.

• Property taxes

• Insurance

• Utilities

• Annual maintenance

• Emergency repairs

• Watercraft costs

• Snow removal

• HOA fees

• Reserve funds for future big-ticket projects

Laying out the numbers allows everyone to answer the real question:

Do we actually want this, and can we realistically afford it, together?

Step 3: Create governance before you need governance

(17:31) Governance is the part families skip because it feels “too formal,” and then they’re shocked when informal arrangements collapse and breed resentment.

This looks like:

• Scheduling rules

• Peak-season guidelines (for example, who gets July?)

• Pet rules

• Guest rules

• Cleaning responsibilities

• Damage protocols

• Maintenance assignments

• A vendor list

• Decision-making authority (for example, who speaks for the group?)

• Rental policies

• Buyout terms

• What happens when someone stops participating?

• How do decisions get made when urgency is involved?

Without governance, the “easygoing sibling” becomes the resentful one and the “flexible one” becomes the doormat. The “organized one” becomes the free property manager. 

And suddenly the family dynamic around the camp has nothing to do with the camp.

Step 4: Do the legally binding planning.

(18:39) Not “what feels fair.” Not “what someone thinks Mom wanted.” You need to do actual legal planning answering these types of questions:

• Should the property be held in a trust?

• Should it be placed in an LLC?

• Should the property be sold at death?

• Should one child inherit it?

• Should multiple children inherit it with buy-out provisions?

• What happens if one child wants out?

• Should spouses inherit a share, or not?

• Should grandchildren be included?

If you don’t create structure, conflict will create its own. And’s it’s never the structure anyone wanted.

Parents think they’re leaving behind a legacy of togetherness. But without a clear legal plan, they can accidentally leave behind a legacy of silence — adult children who stop speaking to each other, grandchildren who lose contact, stories that never get passed down.

No parent wants that. And the good news is that it’s preventable.

(19:44) If you’re interested in learning more about how to legally structure a transfer of your family’s camp, let me know. If enough people want it, I’ll dedicate an entire episode to the mechanics — trusts, LLCs, tax considerations, buyout formulas, all of it. Email me at jill@deathreadiness.com. That’s jill@deathreadiness.com.

As we move into Thanksgiving 2025, I’m thankful for the people who have welcomed me and supported this work. I’m also thankful for the memories from a small town in the Adirondacks that helped shape me. And I’m thankful that those memories are mine to keep, regardless of who ultimately owns the house there.

Maybe you inherit your family camp. Maybe you don’t. Maybe your family decides to sell. Maybe your parents choose something you would not choose.

(20:45) You can still be grateful. Grateful for the memories the place gave you. Grateful for the people who shared it with you. Grateful for the freedom to create something new.

Today we talked about the importance of structure, clarity, and honesty when it comes to the family camp. If you’re not sure whether your estate plan actually reflects those things, I can help.

My Estate Plan Audit will show you what your current plan does, what it doesn’t do, and help you spot the gaps that could turn the place your family loves into the thing that tears them apart.

If you want to stress-test your plan before life forces your family to, check out my Estate Plan Audit at deathreadiness.com/audit. That’s deathreadiness.com/audit. The link is in the show notes.

Thanks for joining me today.

(21:40) This is Death Readiness, real, messy and yours to own. I’m Jill Mastroianni and I’m here to help you sort through it, especially when you don’t know where to start.

Hi, I'm April, Jill's daughter. Thanks for listening to The Death Readiness Podcast.  While my mom is an attorney, she’s not your attorney.  The Death Readiness Podcast is for educational and entertainment purposes only.   It does not provide legal advice.  For legal guidance tailored to your unique situation, consult with a licensed attorney in your state.  To learn more about the services my mom offers, visit DeathReadiness.com.