ChatGPT: Your Virtual Contractor and Legal Assistant
- Peter Civitarese
- Jan 10
- 2 min read

I recently had an issue with a contractor, and I wanted to share how I used ChatGPT to help me resolve it. This experience might inspire you to explore how ChatGPT can assist with everyday challenges.
The Problem
I had an older section of the roof on one of my rental properties that was visibly worn and clearly in need of repair or replacement, so I hired a contractor through Angi's list for the job. However, after the work was completed, the roof actually leaked. Despite several attempts to fix the issue, the contractor failed to resolve it. We mutually agreed that I should seek another contractor for a second opinion. When I requested a refund, the contractor only offered around 50%, which felt unfair given the incomplete and poor-quality of work.
To get a second opinion, I hired a licensed roofing contractor to inspect the work. He sent me photos and explained the issues he saw with the workmanship. I then hired him to fully replace the section of the roof. After the job was done, he provided "after" photos of the new installation.
How ChatGPT Helped Me
I decided to use ChatGPT to see if it could offer insights comparable to those of the licensed contractor. Here's how I did that:
Comparing the Roofs: I uploaded the "before" pictures and called them Roof 1 and the "after" pictures as Roof 2.
Expert Analysis: I asked ChatGPT to act like a roofing contractor with 25 years of experience. I requested it to compare the workmanship and materials used in both roofs.
Results: The AI identified the same issues my licensed contractor had mentioned — poor material use, improper sealing, and overall low-quality workmanship in Roof 1. It provided me an awesome summary.
Taking Legal Action
After gathering this evidence, I used ChatGPT again to help me understand the Massachusetts small claims court process. It provided a step-by-step breakdown using straighforward terminology that was easy to follow. I also asked ChatGPT to draft a Chapter 93A Demand Letter (a formal legal notice for consumer protection issues) and it did an awesome job. I mailed the letter to the original contractor via certified mail. The contractor reached out to me 3-4 days later, having a change of heart. He agreed to fully refund my money. I couldn’t have resolved this so quickly and easily without ChatGPT’s help.

Key Takeaways for You
Leverage AI for Expert Insights: Tools like ChatGPT can deliver in-depth analysis by comparing before-and-after photos and highlighting key issues.
Simplify Legal Processes: ChatGPT can break down complex legal steps like small claims court procedures, making them easier to understand.
Draft Legal Documents: AI tools can help generate well-crafted demand letters and other legal documents.
Enhance Decision-Making: AI can help clarify issues, ensuring you have a well-documented case for negotiations or court proceedings.
If you're facing a challenge, whether with a contractor or other situations, consider how technology like ChatGPT can assist.
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