If you’ve watched Yellowstone, you already know the premise: a powerful family owns a sprawling ranch in Montana. The estate’s sentimental value drives them to do just about anything to keep it in the family.
What unfolds is part Western, part family drama, complete with succession battles, legal fights, emotional blowups, generational loyalty—and disloyalty. Everyone wants to protect the land, but no one agrees on how. The property itself becomes a symbol of identity, legacy, and power.
Most of the families I work with aren’t on 500,000 acres, but the tension and conflict can be exactly the same.
Maybe your family owns a beach house where three generations spent their summers. Maybe it’s a lake cabin with no insulation and a leaky roof. Maybe it’s a few hundred acres of fallow farmland Grandpa used to tend. When a property holds such sentimental value, things have a way of getting expensive.
The Cost of Being ‘Land Poor’
When you’re land-poor, your net worth is tied up in property, but you don’t have the liquidity to maintain it. I’ve also seen this situation described as “land rich, dirt poor,” especially when it comes to family farms.
A great example is a middle-class family that inherits a large estate and finds themselves paying $200,000 a year in property taxes with no rental income and no clear agreement on how to split the costs.
Sometimes, these homes were bought decades ago for a fraction of what they’re worth now. That’s great for appreciation but brutal for taxes and upkeep. The more valuable the home becomes, the harder it is to make group decisions. A brother wants to keep things rustic. A sister wants to renovate. Dad wants to cash out before the next assessment drives the tax bill even higher.
What started as a shared legacy becomes a silent standoff.
Planning for Sentiment
The good news is that there are ways to prevent this kind of breakdown. The trick is to make sure planning happens while the original owners are still alive. If you wait until after a parent passes, you’re dealing with legal logistics on top of grief, family politics, and unresolved expectations.
Here’s what I typically recommend:
- Start the conversation early. Parents need to be clear: is the goal to keep the property in the family or liquidate it for fair distribution?
- If the property is going to be shared, treat it like a business. Set up a family LLC or trust. Decide who will manage it, how decisions will be made, and what will happen if someone wants out.
- Create a maintenance fund. Everyone contributes annually to cover taxes, insurance, and repairs. No more surprise bills or arguments over who paid for the new AC.
I’ve even seen families assign usage rights by season and vote on improvements like it’s an HOA. It’s not glamorous, but it works.
If one sibling wants to own the property outright? That’s fine, too. But make sure it’s documented ahead of time. Structure it as a partial inheritance and adjust the rest of the estate to reflect the buyout. Don’t leave it to your kids to negotiate that on their own.
It’s Not About the Money
The hardest part about sentimental value is that it’s not rational—and that’s okay. You’re allowed to feel attached to the place where your kids learned to swim or where your parents celebrated their 50th anniversary.
But you also have to be realistic. Sentiment doesn’t pay property taxes or replace a roof. It won’t shield your family from hard feelings if the burden isn’t shared fairly.
I’ve worked with clients who made this work beautifully. I’ve also seen families torn apart over a two-bedroom cottage with a busted water heater. The difference always came down to clarity, not cash.
So, if you own a property with emotional attachments and plan to pass it on, don’t wait. Talk to an advisor and an attorney. Most importantly, talk to your kids.
In the end, it’s not the property that causes the damage. It’s the silence around it.