My yearly insurance re-shop, done in one morning with my AI assistant

Once a year I audit the insurance on our rental properties. It is the kind of job that is easy to push to next month: gather the paperwork, write to the brokers, wait, then compare quotes that never line up with each other.

This October I handed most of it to my AI assistant.

The property

It is a five unit rental in Roanoke that I own with partners: two small buildings on one lot. It had ended up on two separate policies with the same insurer. The larger policy had gone up sharply at its last renewal, the deductibles were high, and neither policy had ordinance or law coverage, the part that pays to bring a damaged building up to current code.

What the assistant did

It started with the emails asking our agent for the declarations pages and the loss history. Those came back early on a Tuesday morning. From there it:

• pulled the facts out of those PDFs and wrote one standard quote request
• drafted that request to four insurance agencies and to our current insurer
• read the quotes when the first broker answered, about an hour later
• laid them side by side against what we pay now
• drafted the email to my partners setting out the choice

By lunchtime I had the quotes, the comparison, and the email to my partners.

What I did

I read every email before it went out, and I sent each one myself. The assistant does not send anything on its own. That is a rule I set, not a setting I hope it follows. Another rule: the tax ID goes by phone, never in an email.

The quotes came from a broker and the insurers behind them. My partners and I made the decision.

What came back

The best quote came in $854 a year under what we pay now. It also puts both buildings on one policy, lowers the deductible, and adds the coverage we were missing: ordinance or law, water backup, and mold.

I expected to trade some coverage for the lower price. Here I did not have to.

What this does not show

This is one property and one quote. The new policy is not in force yet. The final premium can still move while the broker and I settle the last details, and our current insurer has not sent its renewal price. None of this is a recommendation about your own coverage.

The part I kept

The assistant also turned the requests into a standard packet I can reuse for any property, every year. Its note on what every broker needs is short: the declarations page, the loss history, and the tax ID, given by phone.

That packet matters more to me than this year's number. Next year the re-shop does not depend on me remembering how I did it.

Bring a real problem

This is the kind of task members bring to the AI Operator Group: the chore you know you should do every year. We work it live, together, with the assistant doing the legwork and you making the calls.

If something like this has been on your list for a while, bring it.