Steadily built a ChatGPT app. Not a chatbot on our website, not a gimmicky AI feature bolted onto the quote flow; an actual app you install inside your ChatGPT workspace that pulls in live data, runs a property analysis, and gives you an instant estimate on a property, factoring in real landlord insurance costs when you're evaluating deals.
If you already use ChatGPT to research markets, run numbers, or draft lease clauses, this plugs directly into that workflow. If you haven't touched ChatGPT yet, this is honestly a solid reason to start.
What the Steadily ChatGPT app does
The app connects your ChatGPT app or browser window directly to Steadily's insurance data. When you ask ChatGPT to evaluate a rental property, it can pull in actual insurance cost estimates for that specific address rather than guessing or spitting out a generic national average. It factors in location, property type, and the landlord insurance coverages that apply to your situation.
You can add the Steadily app to your ChatGPT workspace in about 10 seconds. No API keys, no configuration beyond clicking "add." Once it's installed, just tag @Steadily in your prompts and ChatGPT knows to pull from the app.
Three prompts to try first
You can ask it whatever you want, but these three cover the use cases most landlords actually care about. Copy them, swap in your numbers, and see what comes back.
Prompt 1: Evaluate a rental deal with insurance included
This is the one that saves the most time. Instead of running your deal analysis in one tab and then shopping for an insurance quote in another, you collapse it into a single prompt:
Evaluate this rental deal at [Address]:
Purchase Price: $X
Monthly Rent: $X
Expenses: $X
Include property insurance from @Steadily to tell me the monthly cash flow.
ChatGPT breaks down the deal economics and pulls in an actual insurance estimate for that property. You get cap rate, cash-on-cash return, and monthly cash flow with insurance already baked into the expense line. No more plugging in "$100/month for insurance" as a rough guess and hoping you're close.
Prompt 2: Get an insurance cost breakdown by address
Sometimes you just want to know what landlord insurance will run you on a specific property, and more importantly, why it costs what it costs:
Use @Steadily to estimate landlord insurance for [Address] and highlight any cost drivers.
This one shines when you're comparing two or three properties side by side. Coastal exposure, older roof, wood-frame construction; the app flags what's driving the premium so you can make an informed call. It also breaks out which coverages matter most for your property, whether that's liability protection, loss of rent coverage, or something like storm and hail if you're in a weather-prone area.
Prompt 3: Run a full scenario analysis
For when you want the complete picture modeled out:
Run a scenario analysis for this rental property:
Purchase Price: $X
Monthly Rent: $X
Include taxes, insurance from @Steadily, and maintenance.
ChatGPT builds a full expense model with property taxes estimated from the address, insurance pulled from Steadily, and maintenance reserves calculated as a percentage of rent. Then you can keep going with follow-up questions. "What if rent drops 10%?" "What if I put 25% down instead of 20%?" The insurance figure stays grounded in real data through the entire conversation, which is the part that usually falls apart when you're modeling deals manually.
Tips for sharper results
Like any AI product, Steadily's ChatGPT app has some limitations. Here are some tips to get the most out of the product and ensure it's spitting out the right information:
- Use real addresses. "123 Oak Street, Austin, TX 78701" will get you a much tighter insurance number than "a rental property in Austin." The model calibrates to the specific location, so specificity matters here.
- Put in actual financials. Don't round your purchase price to the nearest $50K. The analysis is only as good as what you feed it, and the insurance estimate calibrates to the actual property value you provide.
- Ask follow-ups. The app stays active through the whole conversation thread. You can say "now compare that to this property at [second address]" and it pulls fresh insurance data without you re-explaining what you want. This is where it really starts to feel like having an analyst sitting next to you rather than toggling between six browser tabs.
Where to get it
The Steadily ChatGPT app is free to use. Head to the ChatGPT app store listing and add it to your workspace. Works with any ChatGPT Plus or Team account.
If you'd rather skip the AI route and just get a quote directly, that works too. A landlord insurance quote from Steadily takes about two minutes and covers single-family rentals, condos, multifamily buildings, and short-term vacation rentals across all 50 states.
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