FROM OUR SENIOR PARTNER CRAIG R. HERSCH:
A few years ago, I sat across from a very successful couple—let’s call them Jim and Carol. They were the classic Gulf Harbour pair: semi-retired, well-traveled, golf handicap proudly in single digits. Their estate plan, they assured me, was simple. “We want everything split equally between our two children,” Jim said, leaning back confidently. “Fifty-fifty.”
They had a lovely waterfront home here in Southwest Florida, a ski condo in Utah, and enough brokerage accounts to keep a CPA busy through the off-season. Their son lived locally. Their daughter lives in New York City. “They get along great,” Carol chimed in. “They always have.”
Fast forward two years after their passing—and suddenly, their kids weren’t speaking.
What happened? The same thing that happens to plenty of families: their kids inherited real estate together. And what once seemed like a sweet, sentimental decision—“They’ll love having the family home!”—turned into a logistical and emotional minefield.
The son wanted to keep the Florida house for family vacations and winter getaways. The daughter wanted her share in cash—because Manhattan real estate waits for no one. Maintenance decisions became arguments. Expenses sparked accusations. And when the local son suggested he should pay “less” to buy out his sister because he was handling all the upkeep, the gloves came off.
If any of this feels uncomfortably familiar, you’re not alone. Estate disputes rarely erupt over stocks or cash. No, it’s almost always the stuff that feels personal. The place where the grandkids took their first steps. Dad’s boat. Mom’s ring. And most especially—real estate. It’s not divisible like an IRA. It’s heavy, rooted, expensive to maintain, and full of expectations.
So what’s the lesson?
Equal isn’t always fair. And fair doesn’t always mean together.
If you’re planning to leave real property—especially a second home or cherished family retreat—you’ve got a few options. And some of them are better than others.
One approach I often recommend is leaving the property to a single heir, while balancing the estate with other assets for the others. Maybe your son truly loves and uses the home—while your daughter would rather have the equivalent value in brokerage assets. That’s fair. Even if it’s not “equal.”
Another option is creating a qualified use trust, or even a family LLC, with clear governance rules. Who makes maintenance decisions? Who pays what? Can one child rent out the property? Can the others object? These questions must be answered up front—because if you leave it to your kids to work out later, they’ll often do it through lawyers, not conversations.
And then there’s the cleanest option of all: sell the property and split the cash.
Now, I know. That might feel cold. Especially if the home holds generations of memories. But ask yourself—do you want your children to remember Thanksgivings on the lanai? Or spend the next ten Thanksgivings arguing over who forgot to pay the property taxes?
Further, with Florida homestead, there are descent and devise rules that one must follow, especially if you’re married and plan to leave the home to the children upon the first spouse’s passing. Florida homestead is also creditor protected, but that protection vanishes if your will or trust directs a sale rather than a distribution to an heir.
The truth is, you don’t need to leave a burden to leave a legacy.
You can leave freedom. Harmony. And yes—still plenty of memories.
Here’s what I always tell clients: If you’re unsure what your kids really want, ask them. Not in vague terms, but clearly: “If we left you the house together, what would you actually do with it?” Their answers may surprise you.
Because while your children may love you deeply, and each other genuinely—money, real estate, and grief can do strange things to people. Especially when those three show up at the same time.
So take some time, talk to your advisor, and think about the plan. The best gifts aren’t always the ones wrapped in sentiment. Sometimes, the greatest act of love is clarity.
And maybe, just maybe, keeping Thanksgiving sacred.