Is Online Estate Planning Actually a Good Idea?
The honest answer is: for some documents, yes; for others, no. A simple will or a basic advance directive, in a state that doesn't require anything unusual, is a reasonable thing to generate with a well-built online tool. A trust, a blended-family estate, or anything involving business ownership is not: that's attorney territory, and treating it as a form-filling exercise is how families end up back in court.
The more useful question for most people isn't "will vs. online tool": it's what happens between having documents and your family being able to use them. An attorney drafts your will; nothing about that process organizes your bank accounts, insurance policies, or the location of the safe deposit box key. That's a separate, ongoing task that has nothing to do with legal complexity.
On AI specifically: a language model can explain what a durable power of attorney is, or draft a rough first pass at instructions for whoever handles your affairs. It cannot notarize a document, know your state's witnessing requirements, or take any responsibility if it gets something wrong; for anything legally binding, that gap matters.
Where a guided tool earns its place is the organizational layer underneath the legal one: keeping the pointers (who your attorney is, where the will is kept, which accounts exist) current and in one place, regardless of whether the documents themselves came from a lawyer or a template.