until ChatGPT pointed out something I completely missed.

On paper, the deal looked fantastic.

• Projected returns ~20%
• Cash-on-cash ~10%
• Attractive purchase price

The numbers were strong enough to move quickly.

Before moving forward, I asked ChatGPT a simple question about the area’s economic development and population growth to get a quick sense of the market fundamentals.

It summarized the trends and even offered to pull comparative sales data, which was exactly what I was planning to check next.

But then it flagged something important.

The property sits in a floodplain and has had flooding events in the past.

That immediately changed how I looked at the deal.

As investors, we all know the diligence checklist:

1. Crime rates
2. Flood zones
3. School ratings
4. Economic drivers — beyond just the numbers.
5. Population Growth

But, while evaluating multiple opportunities, it’s easy to miss one of those boxes.

Today was a good reminder that AI can be a powerful second set of eyes.

It doesn’t replace judgment, advisors, or proper due diligence — but it can help surface risks and questions we might forget to ask.

One simple prompt I now use when reviewing a deal:

“What are the economic trends, risks, and environmental factors that could impact real estate investment in this area?”

Sometimes the best value AI provides is not the answer — it’s the questions it reminds us to ask.

(Sharing a personal experience, not investment advice.)

Curious — are you using AI anywhere in your deal analysis yet?