The Overlooked Challenges in Vacation Rental Property Management

For those of us who have been on the front-line for a while, we know that being a vacation rental property manager isn’t for the faint of heart. With all its moving parts, it can sometimes feel that keeping your head above water is an achievement. 

We’ve all been there. We’ve juggled guest expectations, dealt with regulations and handled the occasional unexpected and bizarre issues. And we are not alone. These challenges are universal and impact every one of us in our industry.

Videos and social media posts suggest we spend more time on design and automating communications, but they are missing the most vital elements that keep a business grounded and thriving.

If guests and owners don’t have Trust in you; if you don’t take Safety seriously; understand the importance of the right Insurance; comply with Regulations, and build Sustainability into your business, no amount of murals or chatbots will save you from potential business failure.

This is where SSTIR Crazy 2025 come in. 

It’s a five-week online event that shines a spotlight on those five essential pillars for success. Neglecting them? Well, that’s just a shortcut to sleepless nights.

Throughout SSTIR Crazy Month, we’ll share some real-world examples of how these challenges show up in our day-to-day operations, the consequences of ignoring them, and how to turn them into opportunities for transformation. You’ll probably recognize many of them. 

Join us, our experts and our fictional property management company StayWise Rentals, as we navigate the problems, resolve the issues and create long-lasting solutions.

Each week, we’ll bring you an issue StayWise Rentals is experiencing, and through podcast episodes, live panels, blog posts, polls and activities, present ways you can avoid the same problems.

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This is not a passive event - there’s plenty of opportunities to be interactive, share your own wins and get expert help.

Week 1: Building Trust—The Secret Sauce for Repeat Bookings

Learn how trust turns first-time guests into lifelong customers and owners into loyal clients.

Airbnb spends billions on building trust with guests and property owners and this is non-negotiable for any rental business. However, many direct book website lack trust signals and don’t share the types of information that encourage guests and owners to trust them.

In Week 1 of SSTIR Crazy Week, Chris Maughan, CEO of I-PRAC, will lead participants through actionable strategies to build direct booking trust and maintain long-term guest and owner loyalty​.

Week 2: Safety First—Because “Accidents Happen” Isn’t a Business Plan

Discover how prioritizing safety protects your guests, your team, and your bottom line.

Safety remains a top concern in vacation rentals. Overlooking minor hazards can lead to serious accidents, legal battles, and increased insurance premiums.  Don’t wait until the disaster happens to appreciate the importance of checks, audits and safety plans.

Justin Ford of Breezeway leads the Safety week, bringing you awareness of risk, and simple ways of making your properties safer places for your guests to stay.

Week 3: Insurance Demystified—What You Don’t Know Can Hurt You

Navigate the world of STR insurance and protect your business from costly surprises.

For anyone who has heard the words, ‘You’ve been served’, the topic of insurance is front of mind, but the insurance landscape for short-term rentals can feel like a minefield. What is clear is that Inadequate coverage can lead to financial ruin if unexpected events occur.

Nick Massey from Proper Insurance will guide you through through avoiding common coverage gaps and safeguarding assets​.  With plenty of real-world examples you’ll discover exactly what you need to keep your business and your assets safe and secure when disaster strikes.

Week 4: Winning the Regulation Game—Stay Ahead, Stay Open

Tackle local laws and compliance challenges with confidence and ease.

Not a week goes by without another region being impacted by regulations, and even those areas that seemed immune to legislative barriers are feeling the pinch.

Municipal regulations are rapidly evolving, requiring STR companies to adapt swiftly to avoid penalties or shutdowns.  There are ways of working alongside even the most restrictive of short term rental laws, and being a part of the process, not a bystander to it.

Dana Lubner from Rent Responsibly will share strategies for navigating regulatory complexities, empowering businesses to remain compliant​.

Week 5: Sustainability Made Simple—Profits and Planet Can Coexist

Explore easy, actionable ways to make your properties eco-friendly without breaking the bank.

Travel data shows that travelers are increasingly favoring eco-conscious accommodations, meaning sustainability is no longer a luxury but a necessity. Going green is no longer a costly option - there are plenty of ways of saving money through eco-friendly practices as well as making a little more as well.

Bob Garner from Environrental will discuss cost-effective ways to integrate sustainability into operations while enhancing guest appeal​.

Preparing for SSTIR Crazy Month: Your Call to Action

SSTIR Crazy Month isn’t just an event; it’s a movement to elevate the standards of short-term rental property management.

By participating, you can:

• Gain expert insights to tackle the most pressing challenges.
• Take part in challenges and activities each week
• Earn badges and leaderboard recognition through gamified activities.
• Win prizes for taking part in activities and games
• Network with peers and thought leaders in the industry.

This isn’t just for business leaders - it’s an event every employee should participate in and learn from.  Getting the whole team on board, sharing what is being learned and putting it into practice could be the kick-start you need for 2025.

Register Now

Signing up for SSTIR Crazy Month shows your commitment to making changes. 

We’ll let you know what’s upcoming each week, the activities, leaderboard challenges, live panels and polls.

Visit Vacation Rental Formula’s SSTIR Crazy 2025 to register today and take the first step toward operational excellence.

Let’s redefine the future of short-term rental management, one foundational pillar at a time.

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