Do you feel stuck with one or two rentals and wonder how to reach $10,000 a month in passive income from your properties? Using ChatGPT as your AI real estate advisor can bridge that gap by giving you strategies tailored to your situation.
Most investors hit this wall. Traditional advice only lists strategies – flipping, syndications, short-term rentals, commercial – but it doesn’t tell you which one fits you. That’s where AI can change the game. Instead of using it to summarize meetings or generate to-do lists, you can use tools like ChatGPT as a trusted advisor.
In this post, I’ll show you how to prompt AI differently using the CRIT system (Context, Role, Interview, Task). This approach takes you from vague ideas to a personalized roadmap for hitting $10K a month.
The CRIT System: Turning AI into a Real Advisor
Jeff Woods, author of The AI-Driven Leader, introduced me to CRIT. It stands for Context, Role, Interview, Task. By layering these steps, you force AI to ask YOU questions before it gives a response.
This is what separates it from 99% of other prompting methods.
- #CONTEXT# Share your real situation here. The more specific and thorough you can be here, the better Chat’s analysis becomes.
- #ROLE# Assign expertise. Here, you instruct the AI on what role it should play. Without an assigned role, it tends to respond as a generalist, not a specialist.
- #INTERVIEW# Now you have it ask you a minimum of 3 questions, but make sure it asks you ONE AT A TIME. This way it can better understand your goals and limitations.
- #TASK# Then you finally tell it to give you the desired output.
Let’s walk through an example together.
Using the CRIT Method to Pick a Real Estate Strategy
This is a real example of what happened when I ran CRIT with ChatGPT to help me buy my “first” real estate property.
Here’s the prompt I gave it so that you have an idea of how it looks:
#CONTEXT#
I’m a software developer making $120,000 a year. I like my job, but I’m tied to a desk all day in the office. I love traveling, and I’m trying to plan a trip to Disney with my family, but I don’t have enough vacation days.
I own 1 rental property and I’ve flipped a few houses and I like the income I get, but 1) I need more time/bandwidth to buy and manage more properties, and 2) I can’t quit my job because it would take too long to acquire enough properties to replace my income.
I don’t want to sacrifice my way of living. I’m looking for a real estate strategy that I can pick up as a full-time worker, that pays me passive income, and replaces my salary in 1–3 years.
#ROLE#
Your role is to act as someone with experience in all fields of real estate, owning 3 of every classification of asset.
#INTERVIEW#
You will ask me 3 questions BUT ASK THEM ONE AT A TIME to gain a deeper context about my situation and experience in real estate so that you can better provide a solution.
#TASK#
Then you will provide me with 3 real estate strategies that would perfectly fit my situation and skillset that I can pursue while still working my developer job, but pay me meaningful passive income so that I can earn $10K/month in passive income.
Try pasting this into ChatGPT yourself and answering the questions!
Here are the questions it asked me and my responses:
1. What type of rental property do you currently own, and how involved are you in managing it?
I own 1 single-family rental right now in addition to my primary residence. I self-manage it. I renovated it when I first bought it. Aside from small maintenance requests, I'm not that involved.
2. How much passive income does it generate, and what are the loan terms?
There are 4 bedrooms, and I rent them out for $925/month after I renovated the property and increased its value. I have a 30-year fixed at 6.76% interest so my monthly payment is $3,243. My net income right now is around $457/month, not including property taxes, insurance, maintenance, and vacancies.
3. How much capital do you have available, and are you open to partnerships or leverage?
I have $50,000 saved up, but I'm only comfortable deploying maybe $20K for training, acquisition, or fees if I know that the strategy will work. I'm also open to partnering with someone who has capital, if that means doing bigger or more profitable deals, and I don't have to do everything. I’m to raising capital, but I’ve never done its, and so I’m not sure how good I would be
This Was ChatGPT’s Response
After asking me questions and responding, the top option was to syndicate small multifamily deals (8–30 units), where I can earn cash flow and equity without handling day-to-day operations.
Coincidentally, that’s already what I do full-time as a real estate investor. I buy and hold multifamily apartments. The Context I gave at the start of my prompt was actually the exact situation I was in before I started doing real estate full-time.
And if I had ChatGPT back then to help, I wouldn’t have done house flips instead.
Looking Ahead to Your Next Steps
Go ahead and try this for yourself! You can either copy and paste what’s above OR fill out the template yourself.
The point of this exercise is to stop asking AI broad questions. Start using the CRIT method: give it context, assign it a role, let it interview you, and then demand a clear task. The results may surprise you.
This article is actually part 2 of 3 about the topic of using ChatGPT to invest in real estate. In my next piece, I’ll find out if I can use ChatGPT to teach me (and you) – very extensively – how to buy an apartment building
You can access Part 3 here. I also have a video series you can watch here.
To your success,
Michael Blank
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