Short Story Series: DIY Will Risks, What Most People Get Wrong

Karunn Shahani

Principal Lawyer and Managing Director

The Situation

A client came in with:

  • A $3M home

  • A $2.1M investment property

  • A will written by ChatGPT

On the surface, the will was technically valid.
It reflected their wishes and had been executed correctly.

But underneath that, there were serious problems.

What We Found

1. The Will Had No Control Over the Properties

Both properties were held as joint tenants.

That meant:

  • The will had no authority over those assets

  • Ownership would pass automatically to the surviving owner

  • What the will said was effectively irrelevant

2. No Enduring Power of Attorney

There was no enduring power of attorney in place.

If the client lost capacity:

  • No one could legally manage or deal with the properties

  • Decisions could be delayed, complicated, or require court involvement

3. A $2.1M Asset Left Directly to a Minor

The will directed the investment property straight to a minor, with:

  • No testamentary trust

  • No asset protection

  • No tax planning

This creates major risks:

  • Income could be taxed at penalty (adult) rates

  • The asset would have no protection from future claims

  • Control over the asset would be limited and potentially mismanaged

The Real Cost of “Saving Money”

The client may have saved a few thousand dollars on estate planning.

But the potential downside?

  • Massive tax inefficiencies

  • Loss of control over key assets

  • Legal complications during incapacity

  • Long-term risk to beneficiaries

The Fix

We stepped back and looked at the full picture, not just the will:

  • How the properties were legally held

  • Who should receive what — and how

  • What happens if something goes wrong before death, not just after

The Takeaway

If You Own Significant Property, Your Estate Plan Must Reflect It

A will on its own isn’t enough.

And a generic document, even if technically valid, can completely miss:

  • Ownership structures

  • Tax implications

  • Asset protection

  • Incapacity planning

That’s where the real risks are.

Wills & Estates

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