Trust Week - Jan 27
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Safety Week - Feb 3
Insurance Week - Feb 10
Sponsored By
Regulations Week - Feb 17
Sustainability Week - Feb 24
SSTIR Crazy Month is an exciting five-week online event designed for short-term rental professionals to tackle the industry's most pressing challenges in Safety, Sustainability, Trust, Insurance, and Regulations (SSTIR).
Guided by expert mentors and brought to life through the engaging story of StayWise Rentals—a fictional property management company navigating these hurdles—participants will gain actionable insights and solutions they can apply to their own businesses.
With gamified elements like weekly challenges, mystery clues, leader boards, and exclusive rewards, SSTIR Crazy Month combines education with entertainment to inspire growth and innovation in the vacation rental industry.
Join us and transform how you manage your rentals!
Join us in a month-long adventure with StayWise Rentals, a fictional property management company navigating the highs and lows of rapid growth. This year, SSTIR Crazy Month 2025 brings you an engaging, story-driven program that mirrors real-world challenges in the short-term rental industry.
StayWise Rentals started as a family business but is now at a crossroads, tackling pressing issues in Safety, Sustainability, Trust, Insurance, and Regulations. Each week, you’ll step into the shoes of Sarah and Mike Chen as they face these hurdles head-on, guided by industry-leading experts. Will they emerge stronger or falter under pressure? You decide!
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Follow StayWise Rentals through weekly episodes highlighting challenges and innovative solutions.
Learn from top minds like Chris Maughan, Justin Ford, Nick Massey, Bob Garner, and Dana Lubner, and others, as they mentor the StayWise team.
Earn badges, solve mysteries, and climb the leaderboard by participating in challenges that reflect real business scenarios. Participate to win some great prizes.
Discover strategies you can implement in your own rental business, from trust-building techniques to sustainability practices.
The story of StayWise Rentals is more than fiction—it’s a mirror of the obstacles and opportunities every rental operator faces. Through engaging content, live panels, Q&A sessions, and challenges, you’ll gain practical knowledge and tools to elevate your business.
Be part of the journey. Be part of the solution. Are you ready to help StayWise Rentals thrive?
Register today and start earning your first badge!
Chris Maughan launched I-PRAC in April 2015 after seeing first-hand the damage that can be inflicted by rental fraud.
Earlier that year, he’d been contacted by a family who had lost £15,000 to online fraudsters and were left stranded without accommodation in Cannes. As well as giving them somewhere to stay – through his other company, AES Accommodation Ltd – Chris also vowed to put an end to rental fraud, a problem that is tarnishing the industry worldwide.
With the I‑PRAC logo becoming a recognized stamp of approval for legitimate rental agencies and property owners worldwide, Chris is keen to keep spreading the message about rental fraud.
If you’d like to organize an interview with Chris, or are looking for a comment or guest article on rental fraud, please get in touch.
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Heather Bayer and Chris Maughan host a great panel discussion with guests, Justine Ireland, and Jill Highsmith McGee, where you will discover how to transform your website into a trust-building powerhouse! Learn essential strategies to boost direct bookings, enhance guest confidence, and create a professional online presence.
StayWise Rentals faces a trust crisis with plummeting direct bookings, website skepticism, and flagged chargebacks. Chris Maughan from I-PRAC shares practical tips to rebuild trust and credibility.
This guide will walk you through the essential trust signals that every vacation rental website should incorporate.
Learn how to create your “About Us” page for your Short-Term Rental direct booking website
Create a powerful vacation rental direct book website by including these trust signals
The core difference between product marketing and trust marketing; and why the latter should not be dismissed
Attract short-term rental guest bookings by mastering the art of story telling
This article will help you answer the most common questions your guests are seeking the answers to, without them having to be asked.
Trust is such a basic tenet in our industry but it’s rarely mentioned. It's the key to mastering a book direct strategy.
Justin Ford, a leading authority on vacation rental safety, is passionate about helping property managers and owners create secure environments for their guests.
With years of experience in the short-term rental industry, Justin has witnessed the serious consequences of overlooked safety protocols. This inspired him to dedicate his career to raising awareness about safety standards and providing practical solutions.
As the Director of Safety & Certification Programs at Breezeway, Justin has worked tirelessly to develop systems that ensure properties meet the highest safety benchmarks.
Whether it’s advising on safety audits or speaking at industry events, Justin is committed to making safety a top priority for the vacation rental community.
To arrange an interview or guest article with Justin on safety in short-term rentals, please reach out.
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Heather & Mike Bayer host an engaging panel discussion featuring Justin Ford, Jessica Duce from J Duce Design and Sarah Karakaian from Thanks for Visiting, where you’ll dive into practical tips for creating secure, welcoming spaces, including smart interior strategies, cutting-edge tech solutions, and proactive safety measures that protect guests and enhance their experience.
In this episode host Heather Bayer sits down with Justin Ford, the Director of Safety and Certification Programs at Breezeway, to discuss the crucial role of safety in vacation rentals and the ongoing SSTIR Crazy safety campaign.
Here are six hidden dangers that might be lurking in your vacation rental
Short-Term Rental safety SOPs and how to create them to protect your guests, team, and properties.
StayWise Rentals take a hard look at current safety practices after an unfortunate accident reveals major weaknesses
Practical tips for short-term rental businesses spot the signs if their properties from being exploited for illegal activities
Minimize the chances of guest injuries at your properties and protect your business
How to perform short-term rental guest screening for multi-properties
Effective guest screening in the digital age: Ensure compatibility, respect privacy.
How to ensure short-term rental guest safety and protect your vacation rental from liabilities
With over eight years at Proper Insurance, and more than a decade in the specialty insurance industry, Nick Massey brings a wealth of expertise to his role as Chief Sales Officer.
Nick specializes in demystifying the complexities of insuring vacation rental properties via educating and consulting with short-term rental owners and property managers.
His extensive background has enabled him to build an exceptional team of agents at Proper Insurance focused on providing clarity and seamless service.
Nick loves engaging with clients, listening to their short-term rental business successes, and offering his insider knowledge to help them protect their properties and succeed in the industry.
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Heather Bayer hosts an insightful panel discussion featuring industry expert Nick Massey from Proper Insurance and Jackie Wolf of Waivo with special guest Madi Johnson from 'For The Love Of Upstate'.
Together, they delve into real-world claims that highlight the importance of comprehensive insurance coverage. From unexpected liability scenarios to damage mitigation strategies, this panel provides actionable insights to help property owners protect their investments and navigate the complexities of short-term rental insurance.
Join Nick Massey from Proper Insurance as he helps StayWise Rentals navigate insurance gaps. Learn how to protect your business, avoid costly claims, and ensure you're always covered.
Are you fully covered? Discover five costly insurance gaps that could sink your vacation rental business and how to protect yourself.
From liability to loss of income, this guide breaks down the 8 critical insurance coverages every short-term rental owner needs
From liability protection to damage waivers and business interruption to travel cover. Make sure your insurance covers everything in this article.
Ultimate short-term rental insurance guide from Proper Insurance: Simplify & protect.
Dana Lubner is a dedicated leader and advocate in the short-term rental (STR) industry.
Her journey began in 2018 at Effortless Rental Group, where she discovered a passion for supporting and strengthening the STR community.
In 2019, she co-founded Mile High Hosts to unite Denver’s hosting community, promote responsible hosting practices, and defend against restrictive regulations.
In 2020, Dana joined Rent Responsibly as Head of Leadership Development, where she supports STR alliances across the U.S. by organizing educational events, connecting leaders with policy experts, and fostering self-sustaining communities.
Under her leadership, the number of alliances nationwide has grown significantly, reflecting her commitment to empowering STR hosts and property managers.
Dana also co-hosts the podcast *How to Save Your Vacation Rental Business* with Matt Landau, providing valuable insights and actionable advice for STR professionals.
Her work continues to inspire the industry, shaping a more responsible and thriving future for short-term rentals.
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Website >>
This panel showcases real-world successes from vacation rental associations that have tackled regulatory challenges. Learn actionable strategies for compliance, advocacy, and building strong community ties.
Join Rent Responsibly's Dana Lubner as she helps StayWise Rentals tackle new regulations. Learn how to build community support, stay compliant, and turn challenges into opportunities. Tune in for expert guidance!
In this guide, we’ll describe what an alliance is, why to start one, and how to start a group in your community.
This guide provides new and experienced advocates with essential tips to participate in advocacy, confidently and successfully.
Chris Maughan launched I-PRAC in April 2015 after seeing first-hand the damage that can be inflicted by rental fraud.
Earlier that year, he’d been contacted by a family who had lost £15,000 to online fraudsters and were left stranded without accommodation in Cannes. As well as giving them somewhere to stay – through his other company, AES Accommodation Ltd – Chris also vowed to put an end to rental fraud, a problem that is tarnishing the industry worldwide.
With the I‑PRAC logo becoming a recognized stamp of approval for legitimate rental agencies and property owners worldwide, Chris is keen to keep spreading the message about rental fraud.
If you’d like to organize an interview with Chris, or are looking for a comment or guest article on rental fraud, please get in touch.
Email >>
Website >>
Learn key terms, effective strategies, and best practices for navigating short-term rental regulations. Connect with decision-makers and influence regulatory decisions in your favour while staying ahead of changes and prepare for the future of regulations.
A great panel discussion and you can now watch to the recording and join industry leaders, Justin Ford, Catherine Ratcliffe, and Humphrey Bowles, who dive into the essential but often overlooked areas regarding safety in the vacation rental industry.
We will notify you of all upcoming events as part of SSTIR Crazy Month 2025 and also your standings in the competition to win our grand prize.