Key Takeaways
- “Outdated” doesn’t just mean old — it also means documents prepared in another state, before a marriage, or before Florida law changed. Any of these can make your plan legally unenforceable.
- An unfunded Trust — or one funded the wrong way for Florida — sends your estate straight into probate, defeating the entire purpose of having a Trust.
- Beneficiary designations feel simple and convenient, but they’re one of the most common sources of estate planning disasters. An ex-boyfriend, a child in a divorce, or a special needs heir can each derail everything.
- DIY documents — including those generated by AI — are built for a general audience. Florida is a legal outlier, and generic documents routinely fail to meet its specific requirements.
- Assuming your family will “figure it out” is how families end up in court, fighting each other, and burning through the inheritance in legal fees.
Most estate planning mistakes don’t announce themselves. They hide in documents that look fine, feel finished, and sit in a drawer for years — right up until the moment someone needs them. That’s when the problems surface, and by then, the options for fixing them are much more limited.
On a recent episode of Trust Me, It’s Complicated, estate planning, probate, and elder law attorney John Marshall of Marshall Law walks through the five biggest estate planning mistakes he sees in his practice — each one illustrated with real cases from clients in The Villages,Wildwood,Leesburg,Lady Lake,Fruitland Park,Minneola,Sumter County, Lake County and Citrus County. His message throughout: these mistakes are fixable — but only if you catch them before they matter.
Mistake #1: Outdated Documents
When most people hear “outdated documents,” they picture a Will that’s forty years old with provisions for children who are now in their fifties. That’s one version of the problem. But Marshall sees several others just as often.
Documents can be outdated because they were prepared in another state. Florida is one of the most distinct legal environments in the country when it comes to estate planning — and that’s not an exaggeration. Marshall practices law in both Ohio and Florida, and he describes them as being on different planets. Most states share a broadly similar legal framework. Florida doesn’t.
One common problem: in Ohio and most other states, a Will is valid upon the person’s death. In Florida, a Will isn’t legally valid until a judge admits it to probate. To do that smoothly, the will needs a self-proving affidavit — an attachment confirming the document was properly executed. Other states don’t typically use them. Without one, the estate must petition the court to appoint a commissioner, locate the original witnesses, take their statements across state lines, and file everything before the Will can even be admitted. That process adds months and costs hundreds or thousands of dollars.
Documents can also be outdated because they were prepared before a marriage or remarriage. A surviving spouse who isn’t mentioned in an estate plan can’t simply be left out. Florida law gives them the right to claim either a pretermitted spouse’s share (50% of the probate estate) or an elective share (30% of the entire estate, including assets passing outside of probate). Which applies depends on the specific facts — but either way, the surviving spouse is protected by law regardless of what the documents say.
Then there’s the issue of law changes that outpace the documents. Marshall shared a case where a client’s Power of Attorney was executed in January 2012 — but drafted using a template that predated Florida’s new power of attorney statute, which took effect on October 1, 2011. That statute required specific powers to be separately initialed, confirming the person understood and was granting those powers intentionally. The old template didn’t include that language.
By the time the document was needed, the client had dementia and couldn’t sign anything new. The result: a guardianship proceeding — the exact outcome a Power of Attorney is designed to prevent. The family went to court anyway, spending time and money that proper planning would have avoided entirely.
Estate planning is not a one-and-done exercise. Marshall notifies his clients whenever a law changes in a way that affects their documents, and aims to review every plan every two to three years. Most firms don’t do that. Which is part of why this mistake keeps happening.
Mistake #2: Unfunded Trusts — and Trusts Funded the Wrong Way
A Trust only works if your assets are actually in it. An unfunded Trust — one that was drafted and signed but never had assets transferred into it — accomplishes nothing. When the person dies, the estate still has to go through probate, because the Trust holds nothing.
Marshall sees this constantly, and he knows exactly which local firm is responsible for most of the cases he encounters. “Every estate that comes to me from that firm requires probate,” he says — because the drafting attorney never once explained to clients that they needed to retitle their accounts, deed their property, or update their beneficiary designations to fund the Trust they paid for.
He’s currently handling a case where an attorney prepared a deed transferring a client’s home into a Trust — but never recorded it. When asked why, the firm’s staff member laughed. “Why would we record that?” The deed is now missing. The original documents are nowhere to be found. Getting a copy admitted to the court would cost more than just going through probate, so that’s where the homestead is headed — despite the client having paid for a Trust-based plan.
But there’s a Florida-specific twist that makes this even more complicated: some Trusts are funded incorrectly for Florida law, even when assets are technically in the Trust.
In Florida, when a married couple owns assets jointly, they hold them as “tenants by the entirety.” That means if one spouse is sued individually, creditors cannot reach the jointly held assets. It’s a powerful protection — and it disappears the moment those assets are transferred into a joint Trust. Once inside the Trust, the couple holds them as “trustee and trustee” instead of a “husband and wife,” and individual creditor protection is gone.
Marshall’s approach for married clients: keep joint assets in both names, make them pay-on-death to the Trust, and let them flow into the Trust at the death of the second spouse. The protection stays intact during their lifetimes, and the Trust governs distribution at death.
The homestead property adds another layer. Florida requires very specific language in a Trust to preserve the homestead property tax exemption when the home is titled to the Trust. Out-of-state Trusts almost never have that language. The safer approach — and Marshall’s standard — is to keep the home in the owner’s individual name and use a Lady Bird Deed to transfer it into the Trust at death. The owner retains full control and all homestead protections during their lifetime, and the Trust takes over cleanly afterward.
Mistake #3: Wrong Beneficiaries
Beneficiary designations are marketed as the simple, fast, probate-avoiding solution. Bankers and financial advisors love them. Marshall’s take: they cause more problems than they solve unless they’re used as part of a carefully coordinated estate plan.
The case that illustrates this best: a young woman with terminal cancer came to Marshall about ten days before she died. She told him she wanted everything to go to her mother and brother. When asked about beneficiary designations on her accounts, she said she didn’t think she had any.
After she died, the IRA went to her ex-boyfriend — who had been married to someone else for four years and had children with his new wife. He was still the named beneficiary. The family wanted to pursue legal action. Marshall had to tell them there was no case. The designation was legally binding. She had simply never checked.
A beneficiary designation also can’t adapt to changing circumstances. If a named beneficiary is going through a divorce at the time they inherit, the inheritance can become a marital asset subject to division. If they’re being sued, creditors can reach it. If they’re receiving means-tested government benefits, an inheritance could disqualify them. And if a named beneficiary predeceases you, the designation may create a gap that no one planned for.
Under Florida law, a divorce automatically treats an ex-spouse as having predeceased you — their designation is voided. But if there’s a legal obligation to maintain the ex-spouse as a beneficiary, the designation must be actively renewed. It doesn’t carry over automatically.
Then there’s the IRA problem. The SECURE Act, passed in 2020, now requires inherited IRAs to be fully liquidated within 10 years — dramatically accelerating income tax compared to the old rules where beneficiaries could stretch distributions over a lifetime. And 42 states don’t protect inherited IRAs from creditors. Only 8 do — and Florida is one of them.
If a beneficiary lives in Connecticut, for example, and inherits a $500,000 IRA while in the middle of a lawsuit, that money is fully exposed to creditors under Connecticut law. But if the IRA is directed through the Trust using specifically crafted language — both in the beneficiary designation filed with the IRA custodian and in the Trust itself — Florida’s protection can follow the asset even to a non-protective state.
One more case: a client had a special needs daughter with a court-appointed guardian named Linda. He had named Linda personally as the beneficiary, reasoning that she knew the money was for his daughter. Marshall stopped him immediately. If Linda gets sued, divorced, or simply decides to spend the money, it’s hers — legally. The daughter has no claim.
The correct solution is a Supplemental Needs Trust (Marshall prefers that term over “special needs trust” because it better describes the purpose: supplementing government benefits, not replacing them). The trust becomes the beneficiary, the money follows the daughter, and it can’t be touched by Linda’s creditors or taken in Linda’s divorce.
Mistake #4: DIY Documents
When someone at a chamber event once challenged Marshall on how he could compete with LegalZoom, he surprised the room: “I love LegalZoom. I’ll make more money cleaning up the mess than if I do it right the first time.” That was true then. It remains true today.
DIY estate planning tools have two fundamental problems. First, they guide you toward what you want — not what’s best or legally sound. If you want to name a guardian as your special needs child’s beneficiary, the software will let you do it without ever raising the concept of a Supplemental Needs Trust. Second, they’re designed for the majority of states, not for Florida specifically.
A client walked into Marshall’s office recently with DIY documents he was told were “Florida compliant.” The Power of Attorney had him initial all the powers that don’t require initialing under Florida law — and failed to have him initial the ones that do. It wasn’t Florida compliant, it just said it was.
AI-drafted documents create the same problem, and it’s getting more common. A man called Marshall’s office wanting the firm to sign and notarize an estate plan written by ChatGPT. They declined — the firm won’t execute documents it didn’t prepare — but the real issue runs deeper than that.
AI searches the internet and aggregates information without distinguishing reliable sources from inaccurate ones. Marshall tracked down an article a client once cited as authoritative: it was written before a Florida Supreme Court ruling, predicted how the court would decide, and was wrong on every point. The Supreme Court ruled the exact opposite. The article is still online, still being cited, and AI has no way to know it’s wrong.
Marshall uses AI in his practice — but in a controlled, specific way. A proprietary tool monitors local court rules across all Florida circuits monthly and flags changes. Lexis AI assists with legal research inside a closed, legally vetted database where every source has passed judicial scrutiny. Even then, he reviews the underlying cases himself, because AI misinterprets conclusions about 25% of the time.
Using AI to draft your own estate documents from the open internet, in a state as legally distinct as Florida, is not a shortcut. It’s a different kind of estate planning mistake.
Mistake #5: Assuming Your Family Will Figure It Out
This one is partly about communication and partly about the decisions people make when they don’t want to think too hard about what happens after they’re gone.
The digital banking shift has made asset discovery dramatically harder. When bank statements arrived by mail, a family could piece together the picture within a few weeks of a death. Now, most statements go to an email inbox — and if no one has the password, no one knows where the accounts are. Marshall sees this regularly, even with older clients who switched to digital delivery for security reasons.
The solution isn’t complicated: family members don’t need to know your balances, but they should know where you bank, who holds your retirement accounts, and how to access your email after you’re gone. The person named as Personal Representative or Successor Trustee should know they’ve been named — ideally before you die, not after.
But the bigger issue is who gets named and what happens when it goes wrong. Marshall described a current case in detail. A father died with a Trust that contained provisions legally impossible to enforce under Florida law. The son appointed as Successor Trustee — a skilled welder, Marshall notes since he hold genuine respect for the trades — had no legal training. When he told his brother the provisions couldn’t be enforced, the brother filed a lawsuit against him for breach of fiduciary duty. That lawsuit will almost certainly fail, but not before both brothers have spent thousands of dollars on legal fees, and the family relationship has been permanently damaged. Marshall’s own client got caught up in it when her name was attached to the suit even though she has no liability in the matter.
The father assumed his kids would work it out. They didn’t. They couldn’t. And the Trust itself contained an unenforceable provision that no attorney ever flagged — because the drafting attorney simply wrote what Dad wanted without asking whether Florida law allowed it.
The Bonus Mistake: Attorneys Who Just Do What You Ask
Marshall added a sixth issue he calls the bonus mistake, and it connects everything else: going to an attorney who functions as an order-taker rather than an advisor.
He’s seen the outcome firsthand. A man told his attorney he wanted his home to go to one son, with his wife and other son disinherited. The attorney drafted it that way. The client died six years later believing his plan was in order.
It wasn’t. Florida law is unambiguous: you cannot disinherit a spouse from homestead property. The wife — estranged for two decades, living in another state — inherited a life estate in the home. She’s now renting it out and keeping all the income. The son the father intended to receive the property can’t take ownership until she dies. The disinherited son came back into the estate because the invalid homestead provision brought the disinheritance down with it.
No one told the client any of this. The attorney wrote what he asked for, took the fee, and sent him home feeling satisfied. A good estate planning attorney should do the opposite — flag what can’t be done, explain why, and offer a legal alternative that actually accomplishes – or at least gets as close as possible to – the client’s underlying goal.
As Marshall puts it: “You need an attorney who’s going to say to you, ‘Hold on. That’s not advisable, and here’s why. But here’s a follow-up solution.'”
Don’t Wait Until You Need These Documents to Find Out They Don’t Work
Every case in this episode follows the same pattern: a problem that could have been caught years earlier — with the right attorney asking the right questions — wasn’t discovered until the moment the documents had to be used. By then, the options were limited, the costs were real, and in some cases, nothing could be done at all.
If your estate plan came from another state, hasn’t been reviewed in several years, relies heavily on beneficiary designations, or was put together by someone who simply wrote what you asked — it’s worth a conversation before you need it.
Attorney John Marshall and the team at Marshall Law help families across The Villages, Wildwood, Leesburg, Lady Lake, Fruitland Park, Minneola, Sumter County, Lake County and Citrus County build estate plans that actually hold up under Florida law — and review existing plans to find the problems before they become permanent.
Call Marshall Law at (352) 432-8859 or schedule a consultation online today. The right time to fix an estate planning mistake is before it matters.