The Boostly Podcast: AI Secrets for Mid-Term Rentals – Dr. Rachel’s Secret for Hosts!
Host: Mark Simpson
Guest: Dr. Rachel (with mention of previous guest Ryan Luke)
Date: September 7, 2025
Episode Overview
In this special "Boost Your Bookings Bootcamp" MTR (Mid-Term Rental) edition, host Mark Simpson invites Dr. Rachel to share her groundbreaking strategies for unlocking stable, lucrative mid-term rental bookings using AI tools—especially a custom-trained GPT model. Drawing on personal experience and industry data, Dr. Rachel reveals how hosts can break out of the OTA (Airbnb, etc.) rat race, reduce stress, and triple their earnings by serving overlooked guest avatars in the mid-term market. This episode focuses on actionable steps, memorable case studies, and a live demo unveiling the power of AI to precisely identify and serve the best guest segments for your location.
Key Discussion Points & Insights
1. The Untapped Potential of Mid-Term Rentals (MTR)
- Problem: Traditional STR hosts focus on short weekend bookings, fight for guests, burn out on turnovers, and deal with frequent guest complaints.
- Opportunity: MTRs attract guests willing to pay 1.5x–3x more for longer stays (30+ days), with less turnover and stress.
- Avatars Beyond Medical Workers: There are at least 56 different guest avatars in the MTR world, ranging from insurance-displaced families to construction crews, academic staff, festival attendees, and more (30:44).
Quote – Dr. Rachel (02:10):
"What if I told you that most short-term rental hosts are fighting over weekend bookings, vacation warriors, and there’s a completely different market paying one and a half to three times more for longer stays? That is our mid-term rentals."
2. Leveraging AI for Mid-Term Rental Market Analysis
- Dr. Rachel’s Custom GPT: She demonstrates a tool that, with just a property address and specs, analyzes the local market and generates a detailed report with top guest avatars, expected budgets, booking channels, and must-have amenities.
- Provides seasonality playbooks and identifies decision-makers (insurance adjusters, HR, project managers) (08:30–13:30).
- Outputs data on market risks, regulations, and profitability ("go or no go" for investment).
Quote – Dr. Rachel (06:46):
"This is where AI becomes your unfair advantage. I'm going to be sharing with you exactly the custom GPT that yielded me these results."
- Live Demos: Dr. Rachel runs the GPT live for both US (Tallahassee, FL) and international markets (Brisbane, Australia), showing it provides:
- Guest profiles: e.g., Amazon construction crews, political staff, academic hires in Tallahassee.
- Essential amenities: Large driveways for work trucks, blackout blinds for shift workers, pet-friendly yards, etc.
- Seasonality playbooks: Clues around when each avatar is active (cyclone season, university semesters, legislative sessions).
Quote – Mark Simpson (24:10):
"Try saying that five times fast... [referring to Rail Riders, Site Supervisors found via GPT] Who are these people!?"
3. Insurance-Displaced Families – The Most Profitable and Reliable MTR Guests
- Insurance companies pay top rates for furnished homes while their clients’ homes are repaired due to accidents, water, or fire damage.
- These bookings can last months, deliver steady income, and are less price-sensitive.
- Real Success Stories:
- Dr. Gabby (Tahoe): Booked $2,400/week for insurance housing from a single inquiry (15:35).
- Dr. Mason (Boise): Won bookings by offering a single-level home, key for mobility-impaired guests.
- Example payout: $14,657.14/month on a single insurance contract.
Quote – Dr. Rachel (14:59):
"That is the strategy. Their homeowner's insurance company pays you month after month after month. And that is the whole strategy."
- Types of Displacement: Man-made (plumbing, fires) and natural (hurricanes, storms), with millions displaced in the U.S. yearly (19:38).
4. Identifying, Serving, and Winning Over Your Local Mid-Term Market
- Avatars are Location-Specific: AI report finds unique, market-specific avatars you likely never considered (e.g., "Rail Riders" in Brisbane; "Orange Vest Road Warriors" in Sarasota).
- Must-Haves: Different for each group—parking for trucks, pet-ready yards, blackout curtains, or luxury kitchen appliances.
Quote – Dr. Rachel (27:59):
"Their must-haves, it’s not saying we need, you know, Instagramable wall. Right. That’s not a must-have. When they’re telling you parking for four trucks is a must-have, it’s definitely a different avatar."
- Less is More: Both in portfolio size and in property decoration.
- No need for Instagrammable walls or “OMG Airbnbs”—homes should prioritize comfort and utility for guests experiencing upheaval.
Quote – Dr. Rachel (26:17):
"Less is more from a portfolio growth perspective, yeah, for sure. And then from a decor perspective, these avatars, you don't need as much either. So both."
5. Proactive Planning, Seasonality, and Calendar Management
- Being reactive leads to missed opportunities.
- Hosts need to plan their calendar for peak periods—block out weeks for mid-term stays, and avoid populating calendars with short stays that prevent long bookings.
- AI can forecast when each avatar is most active.
Quote – Dr. Rachel (43:12):
"How do we want to position ourselves as hosts? We want to be proactive, not just reactive, especially with mid-term rentals."
6. The Power of Relationships & Becoming the “Connector”
- Building connections with local housing agencies, insurance contacts, and other hosts is crucial.
- Sharing leads or overflow bookings with others can establish you as the “go-to” or “connector”—leading to future business and more trust.
Quote – Dr. Rachel (46:11):
"At the end of the day, relationships are key... even if they don't have a property available, they're sending us alternatives. So we never want to close that door because it pays dividends."
- "Be the connector"—if you can't house a guest, refer them to your network.
Quote – Mark Simpson (48:24):
"Your network is your net worth. It's so powerful to be able to have this and do this, and the Boostly community is there..."
Notable Quotes & Memorable Moments (with Timestamps)
- AI as Unfair Advantage (06:46)
"This is where AI becomes your unfair advantage..." - Market Goldmine (05:59)
"We're really sitting on a goldmine and we don't even know it." - Unexpected Avatars in Each Market (24:10)
"Try saying that five times fast... who are these people!?" - Case Studies: Insurance Payouts (14:59, 15:35)
Example: "$14,657.14 per month" for one deal. - Portfolio Philosophy (26:17)
"Less is more from a portfolio growth perspective… you don't need as much [in decor] either." - Host Support Network (46:11)
"Relationships are key... having a network of other individuals you can share deals with puts you in a better position for future outreaches." - The Connector Mantra (48:24)
"Be the connector... you want to not say no, you want to say 'yes, leave it with me,' and just go to town on your network." - AI Use in Everyday Life (42:17)
"When I’m cooking in the kitchen is when all the ideas come in. So then I’ll put on my chat and I’ll go back and forth [with GPT]."
Timestamps for Key Segments
| Time | Segment / Highlight | |--------|----------------------------------------------------------------------------------| | 00:00 | Welcome and setting the stage for the MTR bootcamp & global audience | | 02:10 | Dr. Rachel introduces the MTR opportunity and focus on AI tools | | 05:59 | "Hosts are sitting on a goldmine" - insurance and other avatars | | 08:30 | Live demonstration: Using custom GPT for market/guest avatar analysis | | 14:59 | Insurance-displaced families as the core MTR avatar + powerful real-world cases | | 19:38 | Types and scope of displacements (manmade and natural), scale of opportunity | | 22:03 | Demo: Using GPT on an Australian property address | | 26:17 | "Less is more"–portfolio and decor philosophy | | 30:44 | 56+ MTR niches beyond just medical workers; misconception busting | | 32:14 | Live analysis: Sarasota, FL; how AI finds relevant guest avatars per location | | 36:52 | Real-time AI market research & importance of data citations | | 43:12 | Importance of proactive calendar/planning for MTR bookings | | 46:11 | Relationship building, host networks, and long-term outreach advice | | 49:53 | Uncovering even more guest avatars (e.g., sports teams in Sarasota) | | 51:55 | How to reach Dr. Rachel and where to get her custom GPT tool |
Resources & How to Connect
- Dr. Rachel’s Instagram: @shorttermgems
- Live demo tool & resources: Send Dr. Rachel a DM on Instagram for access to her custom MTR GPT
- Her website: 75gems.com – 75 best STR & MTR markets.
Final Takeaways
- AI is transforming the mid-term rental industry: Hosts can now uncover profitable guest types and engage them with tailored strategies, slashing research time from days to minutes.
- Insurance-displaced families & other MTR guests bring high income, lower turnover, and more stable bookings than STR “party” guests.
- The future is about relationships & being the connector: Build your network and your bookings will follow.
- Action Steps for Hosts:
- Use AI tools to analyze your market and find untapped avatars.
- Tailor your property (and calendar) to those avatars’ needs.
- Join and contribute to host networks—be someone's solution.
- Reach out to Dr. Rachel or Mark for tools and strategies to accelerate your MTR journey.
For more, watch the replay on Boostly’s YouTube channel or connect with Dr. Rachel and Mark Simpson via Instagram for direct access to resources and networking!