Finding the Right Attorney for Estate Planning: Why It Matters More Than You Think

When my family began navigating the complexities of my parent's estate planning, I quickly discovered that finding the right attorney was every bit as frustrating as battling an insurance company. The process was eye-opening — and costly in ways I hadn't anticipated. Not all attorneys are created equal, and in a field as nuanced as estate planning, the gaps in knowledge between one attorney and the next can have enormous financial and legal consequences for your family.

Not All Estate Planning Attorneys Know What You Need:

Estate planning sounds like a straightforward specialty. Write a will, set up a trust, designate beneficiaries. But the reality is far more complex, and many attorneys who list "estate planning" among their services may lack deep expertise in the areas that matter most for your specific situation.

One glaring example is the “Caregiver Child Exemption” — a provision that many families desperately need but that surprisingly few attorneys can navigate confidently.

Here's the scenario: an adult child moves into their aging parent's home to provide care, keeping the parent out of a nursing home for two years or more. Under the Caregiver Child Exemption, the parent's property can be gifted to that child without triggering the Medicaid look-back penalties that would otherwise apply to such a transfer.

It sounds like a lifeline — and it is. But it comes with serious, permanent stipulations that an attorney must be able to explain clearly:

- The gift cannot be undone. Once the property is transferred, you cannot reverse it.

- The parent no longer owns the asset. This affects their financial picture entirely, including any future eligibility determinations.

- Strict documentation is required to prove the caregiving relationship met the necessary qualifications.

If your attorney doesn't know this provision exists, or fumbles the execution, your family could face Medicaid penalties, unexpected tax consequences, or lose the home entirely.

The Frustrating Reality of Finding the Right Fit

The search itself can be an ordeal. Here is what many families encounter:

Scheduling barriers. Some attorneys require one to two weeks just to schedule an initial phone call. For families dealing with an aging parent's declining health, time is not always a luxury.

Lack of follow-through. More than once, an attorney promised to "do some research and get back to you" — and never did. That kind of silence is not just unprofessional; it signals that the attorney may not have the experience your situation requires.

Reluctance to work with Medicaid cases. Some attorneys will not take on estate planning work if another party has already been involved in helping a parent qualify for Medicaid. Rather than viewing that as useful groundwork, they treat it as a complication they'd rather avoid.

After working through four attorneys who each left us with more questions than answers, I finally found the right one — and I knew it almost immediately.

How to Recognize the Right Attorney

The turning point wasn't a polished website or an impressive credential list. It was the conversation itself.

When I explained what our family needed, the right attorney did something the others hadn't: he asked questions. Specific, informed questions. He wanted to know which documents were already in place, what work had been done, and what the current structure looked like before offering any direction. He was building a complete picture rather than selling a standard solution.

That instinct — to understand before advising — is the mark of an attorney who actually knows the territory.

The IRS Ruling on Stepped-Up Basis: What the Wrong Attorney Will Never Tell You

Here is the detail that, frankly, stunned me: not one of the four previous attorneys had mentioned a critical IRS ruling on “stepped-up basis” as it applies to trusts.

Let me explain why this matters enormously.

When a property is inherited, the “stepped-up basis” rule resets the property's cost basis to its fair market value on the date of the owner's death. This means that if an heir later sells the property, capital gains taxes are calculated only on appreciation that occurred ‘after” they inherited it — not from the original purchase price decades ago.

Without this protection, the tax exposure can be staggering. Imagine a parent who purchased a home for $40,000 in 1975. That home is now worth $300,000. If the property passes without the benefit of stepped-up basis, the heir selling it could owe capital gains taxes on $260,000 of gain.

With stepped-up basis applied correctly through proper trust structuring, that gain essentially resets to zero at the time of inheritance.

A recent IRS ruling has clarified and, in some cases, limited how stepped-up basis applies to assets held in certain types of trusts. The specifics matter — and structuring a trust incorrectly to sidestep this ruling can cost a family tens of thousands of dollars in unnecessary taxes.

This is the kind of knowledge that separates a genuinely experienced estate planning attorney from one who merely offers the service.

What to Look for When Searching for an Estate Planning Attorney

Based on this experience, here are the questions worth asking before you commit:

1. Are you familiar with the Caregiver Child Exemption, and have you successfully executed transfers under it?

2. How do you handle estate planning when Medicaid planning has already taken place?

3. What is your current understanding of stepped-up basis rules for trust assets following recent IRS guidance?

4. What is your typical response time for client follow-up?

5. Can you walk me through what documents you would want to review before advising us?

The last question is particularly telling. An attorney who asks to understand what's already in place before recommending anything is far more trustworthy than one who immediately pitches a standard package.

The Cost of Settling for the Wrong Attorney

Estate planning mistakes are not always immediately visible. They surface later — when a parent passes, when a property is sold, when a Medicaid application is reviewed. By then, the options for correction may be limited and the financial consequences severe.

The right attorney is not necessarily the most expensive one, the most prominent one, or the one who can see you the soonest. The right attorney is the one who knows enough to ask the right questions — and who has the experience to anticipate the issues you don't even know to ask about yet.

Don't settle. The stakes are too high.

Keep Searching Until You Find the Attorney Who Sees the Whole Picture

My strongest advice to anyone starting this process is simple: keep searching. Don't settle for an attorney who only answers the question in front of them. The right attorney wants to understand the full picture — your family's history, your assets, your long-term goals — and then offers solutions you didn't even know were possible.

One of the most valuable things I learned through this process is that not all trusts are equal, and a trust that was set up years ago may no longer be the best structure for your situation today. That doesn't necessarily mean scrapping everything. It may make sense for some assets to remain in an existing trust while establishing a new “generational trust” to better serve the rest. A generational trust is designed to pass wealth across multiple generations in a way that protects assets from estate taxes, creditors, and the complications that can come with direct inheritance.

The right attorney won't assume the documents already in place are the right ones to keep. They'll evaluate what exists, explain the tradeoffs honestly, and help you decide what serves your family best going forward.

Equally important is how that attorney approaches the conversation around goals. They should be asking:

- What is the long-term purpose of the trust? Is it to protect assets for a surviving spouse? To ensure grandchildren have resources? To minimize tax exposure across generations?

- What do other family members want? Estate planning rarely affects just one person, and an attorney who ignores the broader family dynamic is setting the stage for conflict later.

The best estate planning is not a transaction — it's a strategy. And it takes an attorney who is genuinely curious about your family's future, not just efficient at processing paperwork, to get it right.

If your family is navigating parent care, Medicaid planning, or property transfers, consult with an estate planning attorney who has specific, demonstrable experience in elder law and caregiver exemptions. The difference between the right attorney and the wrong one could be measured in your family's financial security for years to come. 

I am not an attorney and this is not legal advice, sharing experience only. 

Copyright 2026 by Christine E. Smart

Designing Moves LLC 309 7th Avenue, Suite 2

Marion, IA 52302 (by appointment only)

319-377-6891

christine@designingmoves.com

www.designingmoves.com