Prompt library | Short-term rental property evaluation
Evaluate a short-term rental property with AI, in 8 steps.
Ready-to-copy prompts for ChatGPT, Claude or Gemini. Check legality, demand, comps, income, expenses and risks before you talk to a professional.
Works with any AI assistant
Income projection
3 scenarios: conservative, moderate and optimistic
Create conservative, moderate, and optimistic income projections for a short-term rental property located at [ADDRESS], featuring [X] bedrooms, [X] bathrooms, and accommodating [X] guests. Estimate the Average Daily Rate (ADR), monthly occupancy rates, booked nights, and gross monthly and annual rental income.Account for seasonal fluctuations in demand and pricing.Do not present these projections as guaranteed income. Clearly explain the assumptions, methodology, and data used to develop each scenario.
How it works
From an address to a preliminary evaluation
Copy the prompt
Follow the steps in order, from 1 (legality) to 8 (final evaluation).
Add your details
Replace anything in [brackets]: address, price, bedrooms and guests.
Paste and verify
Use it in your AI assistant and confirm the results with official sources and an expert.
The library
8 prompts to evaluate a short-term rental
Each step feeds the next. At the end, the AI rates the opportunity as Favorable, Needs further analysis or High risk.
Legality
Short-term rental rules
Confirm whether the address can operate as a short-term rental: city, county, zoning, licenses and HOA rules.
Act as a real estate analyst specializing in short-term rentals...
Act as a real estate analyst specializing in short-term rentals. Evaluate whether the property located at [ADDRESS] can legally operate as a short-term rental. Analyze applicable city and county regulations, zoning requirements, licensing and permit obligations, rental restrictions, minimum stay requirements, and, if the property is a condominium, any known building or Homeowners Association (HOA) rules and restrictions. Clearly distinguish between confirmed information and details that require further verification. Do not assume that Airbnb or VRBO rentals are permitted simply because active listings exist in the building. Identify the specific documents, permits, regulations, and official government sources that should be reviewed before purchasing the property.
Demand
Demand and market
Analyze tourist and business demand, seasonality and what draws guests to the area.
Analyze the short-term rental market surrounding [ADDRESS]...
Analyze the short-term rental market surrounding [ADDRESS]. Evaluate tourism and business travel demand, seasonality, location, accessibility, nearby attractions, beaches, convention centers, hospitals, airports, and other key demand drivers. Identify the advantages and disadvantages of this location for a short-term rental (STR) investment. Use recent and reliable market data whenever available, and clearly distinguish between verified information and estimated figures.
Comps
Comparable properties
Find similar properties by location, size and amenities to estimate nightly rate and occupancy.
Analyze comparable short-term rental properties similar to...
Analyze comparable short-term rental properties similar to [ADDRESS / UNIT TYPE]. Identify properties with comparable characteristics, including location, size, number of bedrooms and bathrooms, guest capacity, property quality, amenities, and views.nEstimate a reasonable range for the Average Daily Rate (ADR) and occupancy rates based on relevant market comparables.nDo not rely exclusively on the highest-priced listings, as they may not accurately represent typical market performance. Clearly explain how the comparable properties were selected and identify any differences that could affect rental rates, occupancy, and overall investment performance.
Projection
Income in 3 scenarios
Estimate rate, occupancy, booked nights and gross income in conservative, moderate and optimistic scenarios.
Create conservative, moderate, and optimistic income projections...
Create conservative, moderate, and optimistic income projections for a short-term rental property located at [ADDRESS], featuring [X] bedrooms, [X] bathrooms, and accommodating [X] guests. Estimate the Average Daily Rate (ADR), monthly occupancy rates, booked nights, and gross monthly and annual rental income.Account for seasonal fluctuations in demand and pricing.Do not present these projections as guaranteed income. Clearly explain the assumptions, methodology, and data used to develop each scenario.
Expenses
Operating expenses
Calculate HOA, taxes, insurance, utilities, platform fees, cleaning, maintenance and a furniture reserve.
Estimate the expenses associated with operating the property located at...
Estimate the expenses associated with operating the property located at [ADDRESS] as a short-term rental. Include HOA fees, property taxes, insurance, electricity, internet, water, property management fees, booking platform commissions, cleaning costs when paid by the owner, maintenance, repairs, supplies, licensing fees, furniture replacement reserves, and any other relevant operating expenses. Clearly distinguish between known expenses and estimated costs, explaining the assumptions used for each estimate. Avoid overlooking or excluding expenses that could artificially inflate the property’s projected profitability.
Analysis
Financial analysis
Get NOI, cap rate and cash flow at the purchase price, with or without financing.
Conduct a preliminary financial analysis for the purchase of...
Conduct a preliminary financial analysis for the purchase of the property located at [ADDRESS] for $[PURCHASE PRICE] as a short-term rental investment. Using the provided or estimated income and expenses, calculate gross rental income, operating expenses, estimated Net Operating Income (NOI), capitalization rate (cap rate), and cash flow. If financing is involved, incorporate the down payment, interest rate, loan term, and estimated mortgage payments. Present three financial scenarios: conservative, moderate, and optimistic. Clearly show the formulas, assumptions, and methodology used in each calculation. Distinguish between verified data and estimates, and do not fabricate or assume information that is unavailable.
Risks
Risks and stress tests
Look for reasons it could be a bad investment and simulate drops in occupancy and rates.
Act as an independent real estate investment analyst and identify...
PAct as an independent real estate investment analyst and identify reasons why the property located at [ADDRESS] might NOT be a good short-term rental investment.Evaluate potential risks, including regulatory changes, building rental restrictions, increasing HOA fees, special assessments, property taxes, insurance costs, market competition, declining occupancy rates, falling Average Daily Rates (ADR), seasonality, and dependence on booking platforms. Conduct a financial stress test by reducing occupancy rates and ADR while increasing operating expenses to assess the property’s performance under unfavorable market conditions. Identify which variables pose the greatest financial and operational risks to the investment.Clearly explain your assumptions, quantify potential impacts whenever possible, and distinguish between verified information and estimates.
Final evaluation
Preliminary verdict
Bring it all together and rate the opportunity: Favorable, Needs further analysis or High risk.
Act as an independent real estate investment analyst...
Act as an independent real estate investment analyst specializing in short-term rentals (STR). Consolidate all available information about the property located at [ADDRESS] and prepare a comprehensive preliminary evaluation of its potential as a short-term rental investment. Your analysis should cover the following eight areas: 1. Legal Compliance and Regulations: Evaluate applicable laws, zoning requirements, licensing obligations, minimum stay restrictions, and condominium or HOA regulations. 2. Market and Demand: Analyze local tourism and business travel demand, seasonality, location advantages, competition, and market trends. 3. Comparable Properties: Identify relevant short-term rental comparables and explain how their characteristics and performance compare with the subject property. 4. Estimated ADR and Occupancy: Provide reasonable Average Daily Rate (ADR) and occupancy estimates based on available market data and comparable properties. 5. Revenue Projections: Estimate monthly and annual gross rental income under conservative, moderate, and optimistic scenarios. 6. Operating Expenses and Profitability: Evaluate operating costs, estimated Net Operating Income (NOI), capitalization rate (cap rate), and potential cash flow, including financing costs when applicable. 7. Investment Risks: Identify regulatory, financial, operational, and market risks that could negatively affect investment performance. 8. Outstanding Information and Verification: Identify missing information, unverified assumptions, and documents requiring further investigation before purchasing. Final Investment Assessment Conclude by classifying the investment opportunity into one of three categories: * Favorable: The available evidence supports a potentially attractive investment opportunity. * Requires Further Analysis: Additional information or verification is necessary before reaching a reliable conclusion. * High Risk: Significant legal, financial, operational, or market concerns could negatively affect the investment. Clearly explain the reasoning behind your classification, highlighting the most important factors influencing your assessment. Throughout the analysis, clearly distinguish between verified facts, estimates, and assumptions. Do not fabricate missing information or present projected returns as guaranteed. Important Disclaimer: This evaluation is preliminary and does not replace professional due diligence. Before making an investment decision, verify all relevant information through official sources and consult qualified real estate, legal, tax, and financial professionals.
Core principle
AI is the starting point, not the final decision.
These prompts are designed to facilitate a preliminary evaluation of real estate investments, helping you identify opportunities, assess risks, and better understand a property’s potential.
However, artificial intelligence may generate incomplete, outdated, or inaccurate information. Therefore, its results are not a substitute for professional due diligence.
Before investing, verify all information through official sources and consult with an experienced real estate professional, an attorney, and an accountant to confirm the investment’s legal, financial, and operational feasibility.
Our goal is to help you make better-informed investment decisions, not to replace the judgment and expertise of qualified professionals.
Remember: A successful investment begins with reliable information and responsible analysis..
Frequently asked questions
Which AI do they work with?
Any chat assistant: ChatGPT, Claude, Gemini or similar. Assistants that can search the web give more up-to-date results.
In what order should I use them?
From 1 to 8, in the same conversation, so each step builds on the one before.
Do they replace a professional?
No. They help you decide whether a property is worth a closer look. The final decision requires professional verification.
Who created this library?
50 experts. More than 100 years of combined experience. This library draws on the knowledge of 50 short-term rental specialists whose combined experience exceeds 100 years.