Do I need a will if I have a trust?

Yes. Even with a living trust, you need a pour-over will to capture any assets that weren't transferred into your trust during your lifetime. Without one, those assets pass through Oregon's intestacy laws rather than according to your wishes.

What is the difference between a will and a living trust?

A will takes effect at death and must go through probate before assets are distributed. A living trust takes effect immediately, avoids probate, and allows for faster, private transfer of assets to your beneficiaries. Trusts also provide better protection for blended families and beneficiaries who are minors or have special needs.

How much does estate planning cost in Oregon?

Track Town Law offers flat-fee estate planning services in Oregon and Idaho. Fees vary based on the complexity of your plan — whether you need a simple will package, a full revocable living trust plan, or a more complex plan involving Medicaid planning or special needs considerations. Consultations are free.

Do I need an LLC for my small business in Oregon?

Most small business owners in Oregon benefit from forming an LLC. It separates your personal assets from business liabilities, can provide tax flexibility, and signals credibility to clients and vendors. The key is not just forming the LLC but setting it up correctly with an operating agreement, a dedicated bank account, and an EIN.

What does Medicaid planning involve?

Medicaid planning involves structuring your assets and income to qualify for Oregon Medicaid long-term care benefits while protecting as much of your estate as possible. This may involve Medicaid Asset Protection Trusts, spousal protection strategies, and coordinating with VA benefits if applicable. Planning works best when started at least five years before care is needed.

Can I work with Track Town Law if I don't live in Eugene?

Yes. Track Town Law is a fully virtual firm serving clients throughout Oregon and Idaho. All meetings are conducted by video or phone, and documents are signed electronically. You never need to come to an office.

What is Oregon's estate tax threshold?

Oregon imposes its own estate tax with a threshold of $1 million — significantly lower than the federal exemption of $15 million. This means many Oregon families who wouldn't owe federal estate tax may still owe Oregon estate tax. Proper planning with trusts and other strategies can reduce or eliminate this exposure.

How do I get started with Track Town Law?

Start with a free consultation. You can book online at tracktownlaw.com/book-now. Consultations are conducted by video or phone and typically last 25 minutes. There is no obligation and no charge for the initial meeting.

Should You Use AI to Write Your Will or Estate Plan in Oregon?

Oct 13

Written By Jared Hight

Serving Oregon, fully virtual.

People are asking chatbots to write their wills. I understand why. The tool is free, it is fast, and it produces something that looks exactly like a will. It has headings, numbered articles, a signature line, and a confident tone. For a lot of people that output feels like the problem is solved.

It is not. I want to walk through why, because the reasons are specific to how these tools work and specific to Oregon law, and they are different from the reasons I gave in my earlier post on DIY wills in Oregon.

The document is not the plan

Start with the thing nobody tells you: a will is only a will after it is signed correctly. In Oregon that means a paper document, signed by you in front of two witnesses, who then sign it themselves. There is no handwritten exception here, and since January 1, 2026 the statute says in so many words that an electronic record, document, or image does not count as a will. A PDF the chatbot produced, saved to your laptop with a typed signature, is not a will. Printed and signed alone at your kitchen table, it is still not a will.

Oregon does have a safety valve that lets a court accept a defective document if someone proves by clear and convincing evidence that you meant it as your will. A will goes through probate either way. The difference is that a properly signed will is admitted as a matter of course, while a defective one adds a petition on top of the probate, with notice to everyone who would inherit without it and a window for them to object. That has to be argued and won after you are gone, by people who may not agree with each other.

The same gap shows up across the rest of the plan. An Oregon advance directive has to substantially follow the state's form and be either witnessed by two adults or notarized. A transfer-on-death deed does nothing unless it is recorded in the county where the property sits before you die. A revocable living trust in Oregon protects nothing until your house and accounts are actually retitled into it. A chatbot can describe all of this if you ask the exact right question. It cannot make any of it happen, and it does not warn you that the paper it just handed you is inert.

It answers the question you asked, not the one you needed

This is the deeper problem. An AI tool is built to give you what you asked for. If you ask for a simple will leaving everything to your two kids, you get a simple will leaving everything to your two kids. It will not ask whether one of those kids is on disability benefits that an outright inheritance would cut off. It will not ask whether this is a second marriage and whether your spouse's children are in the picture. It will not ask whether your mother is likely to need long-term care in the next five years, which is the question that decides whether a gift today becomes a Medicaid penalty tomorrow.

It will not ask whether the retirement account and the life insurance policy have beneficiary designations that override the will entirely, which they do. It will not ask what the house is worth, so it will not tell you that Oregon's estate tax starts at one million dollars and that a paid-off home plus a retirement account in this state puts a lot of ordinary families over that line.

When I meet with a client, most of the value is in the questions. The documents are the output of those questions. A tool that skips the questions produces a document that answers a problem you may not have.

It will be wrong, and you will not know

Everyone who uses these tools has seen them state something false with total confidence. In most contexts you catch it because you know the subject. In estate planning you are using the tool precisely because you do not know the subject, so there is nobody to catch it.

I have seen these tools cite Oregon statute sections that do not exist, describe the law of another state as if it were Oregon's, and give execution instructions that would be valid in California and void here. They are trained on the whole internet, and most of the internet's estate planning content is about other states, or about federal rules that do not touch the Oregon estate tax at all. The model does not know which parts apply to you. It averages.

A form from a document mill has the same problem, but at least the form was written once by a person and then stayed put. A chatbot drafts fresh every time, and the errors are different every time.

There is no one to call

A will drafted by a lawyer comes with a lawyer. When your bank will not accept the durable power of attorney in Oregon that the chatbot wrote, or the county recorder rejects the deed, or your successor trustee opens the binder after your death and cannot tell which version was final, there is someone whose job it was to get this right and who can fix it.

With an AI draft there is nobody. The company's terms of service say the output is not legal advice and that you use it at your own risk. Nothing you typed into the tool was confidential. There is no file, no notes, no record of what you were trying to accomplish, which is exactly what a court will want to know if the document is ever challenged.

What AI is actually good for here

I am not telling you to avoid these tools entirely. They are good at explaining vocabulary. If you do not know what a pour-over will is or why someone would put a house in a trust, ask the chatbot and you will get a serviceable explanation. Use it to prepare for a consultation. Come in with better questions. That is a real use.

The line is drafting. The moment the tool starts producing a document you intend to sign, you have left the area where it is useful and entered the area where it is dangerous, and there is no signal inside the tool that tells you where that line was.

What the fee buys

My estate planning is flat-fee, fully virtual, and priced on the pricing page. The Essentials Plan for Oregon estate planning exists for exactly the person who was about to ask a chatbot instead. What the fee buys is not the paper. It is the questions I ask before any paper exists, the Oregon-specific judgment about what your situation calls for, a signing arranged so the documents are valid the day you sign them, and a lawyer who is still here afterward.

If you are weighing it, the free estate planning or elder law consultation costs nothing and ends with a written summary of what I think you need and what it would cost. That is a better first step than a prompt.

Bottom Line

An AI tool can write something that looks like an Oregon will. It cannot ask the questions that determine what your plan should be, it does not know which of its own statements about Oregon law are false, and it cannot get the document signed, witnessed, recorded, or funded in the way the law requires. The result is a file on your computer that feels like protection and is not.

Book a free consultation here.

This post is for general information and is not legal advice for your situation. Reading it does not create an attorney-client relationship.