How to Support Your Loved One in Estate Planning
Clarity is kindness.
Last month, we wrote about the subtle signs that surface during holiday gatherings—the offhand comments, the exhaustion after hosting, the gentle clues that it might be time for someone you love (or for you) to consider downsizing.
Many of you reached out afterward with a version of the same question: “Okay, I see the signs. Now what? How do I actually help without overstepping?” That’s what we want to talk about today; because if downsizing is part of the conversation, estate planning usually needs to be part of it too.
Estate planning isn’t just a single conversation. And it isn’t just paperwork. It’s an act of love. It’s clarity. And clarity is kindness. If you and your loved ones are ready to move forward, here’s how to do it with grace.
Why This Matters More in the Lakes Region
Estate planning protects families from having to make impossible decisions during some of the hardest moments of their lives. It removes guesswork. It prevents conflict. And it honors what the person you love actually wants—not what someone assumes they’d want.
Here in the Lakes Region, this sometimes gets even more complicated. Many families own multiple properties—a primary home, a lake house, maybe land that’s been in the family for generations. Some are relocating here for retirement. Others are navigating the transition from full-time resident to snowbird.
When there are properties in multiple states, unclear titles, or family cabins with sentimental weight, the stakes get higher. The conversations may need to take into account many different perspectives. And the need for a solid plan becomes essential.
What “Support” Actually Looks Like
Once the conversation is open, your role is to be a partner—not a director. Here’s how:
Listen more than you direct.
This is their plan, not yours. Even if you have opinions (and you will), your job is to help them articulate what they want. Gently remind other family members of this, too, but not in ways that harm relationships.
Offer to help with logistics.
Finding an attorney, scheduling appointments, gathering documents—these are concrete ways to take pressure off without taking control. But remember, you’re acting in service to the decision makers, so go at their pace.
Be patient with resistance.
Some people need time. That’s okay. Plant the seed, revisit it gently, and trust that they’ll move forward when they’re ready.
Practical Steps to Take Together
Here’s what the process actually looks like when you’re ready to start.
1. Gather key documents.
You’ll need:
Property deeds and titles
Bank account information
Insurance policies (life, health, long-term care)
Retirement accounts and investment statements
Digital account information (passwords, online banking, etc.)
Existing wills or trusts (even if they’re outdated)
This step alone can feel overwhelming—but just getting it all in one place is progress.
2. Find a local estate attorney.
Not all attorneys specialize in estate planning, and local expertise matters—especially in New Hampshire, where laws around property transfer, taxes, and probate differ from other states. Here’s some of what makes estate planning in NH unique:
No state estate tax. New Hampshire doesn’t have an estate tax (though federal estate tax still applies for larger estates).
Property transfer considerations. If you own multiple properties—especially in different states—transferring ownership can get complicated. A trust can help streamline this.
Medicaid planning. If long-term care is a concern, planning ahead can protect assets and ensure eligibility.
Lake property and family cabins. These often carry emotional weight and complex co-ownership dynamics. Who inherits? Who maintains it? Who pays taxes? These need clear answers.
If you need a referral, we’re happy to connect you with attorneys we trust.
3. Discuss the big questions.
These are the decisions that matter most:
Who should make medical decisions if they can’t?
Who will handle finances and legal matters?
What happens to the house(s)?
Are there specific items with sentimental value? (The lake house keys, the dining room table, the quilts your great grandmother made—these things carry weight.)
What are their wishes for end-of-life care?
These aren’t easy questions. But answering them now means nobody has to guess - or argue over them - later.
What Happens to the House?
This is where a lot of families get stuck—and it’s where our real estate experience becomes especially helpful.
There’s no one “right” answer. It depends on family dynamics, finances, and what the person you love actually wants. Here are the most common options:
Keep it in the family.
Sounds simple, but ask the hard questions: Who will live there? Who will pay property taxes and maintenance? Who will be able to use the house, and when? What if one sibling wants to sell and another doesn’t? Without a plan, keeping the house can create conflict instead of preserving memories.
Sell it.
When? Before they pass, or after? If it’s sold before, they can use the proceeds to fund their next chapter—whether that’s a smaller home, assisted living, or travel. If it’s sold after, the estate will handle it—but that means navigating probate, cleanouts, and real estate transactions during grief.
Create a trust.
A trust keeps the property out of probate, which means a smoother, faster transfer. It also gives more control over how and when the property is distributed.
Work with an Attorney to establish Life estate.
They retain the right to live in the home for the rest of their life, but ownership automatically transfers to heirs upon death. This avoids probate and gives clarity—but it also locks in decisions that can’t easily be changed.
We’ve worked with families through all of these scenarios. There’s no perfect path—just the one that fits your family best. And if questions come up, we’re here to help you think through the options without pressure.
After the Documents Are Done
Estate planning isn’t a one-and-done conversation or set of actions. Here’s what happens next:
Store everything safely—and tell people where it is.
A plan doesn’t help if no one can find it. Keep originals in a fireproof safe or with an attorney. Make digital copies and share them with your executor or a trusted family member. Consider using a password manager (like 1Password or LastPass) so loved ones can access critical accounts if needed."
Review every few years.
Life changes. Marriages, divorces, births, deaths, moves—all of these can affect your estate plan. Set a reminder to revisit it every 3–5 years.
Keep communication open.
Estate planning works best when it’s not a secret. Let the people involved know what the plan is—not every detail, but enough that there won’t be surprises.
This Isn’t About Being Morbid
If the holidays revealed signs that someone you love might be ready for a smaller, easier home—or if you’ve been carrying the quiet worry that “we really need to get things in order”—now is the time.
Not because anything bad is imminent. But because the best gift you can give each other is clarity.
Estate planning isn’t about death. It’s about making sure the people you love are cared for, your wishes are honored, and your family can focus on grieving—not guessing.
And if questions come up about the real estate side of things—what selling a home as part of an estate involves, how to prepare a property for sale, what happens with co-owned lake houses—we’re always here to help you think through it.
You don’t have to figure this out alone.
Here’s to life between the lakes and the mountains.
🍁 Keys to the Lakes
— Jenn & Andrea
Have questions about how property transfers work in NH, or what selling a home as part of an estate involves? Email us at Keystothelakesnh@gmail.com or leave a comment. We're happy to walk you through it, no pressure."
