Preliminary Agenda Topics

As the vacation rental industry matures and guest expectations rise, delivering a flawless stay is no longer enough. True differentiation now lies in how brands respond when things go wrong. In this session, Steve Schwab, CEO of Casago, explores how a culture of care, empowered local teams, and thoughtful service recovery can transform negative moments into lasting loyalty. Drawing on his experience Steve will share how operators can strengthen guest relationships, foster trust, and build resilience in an increasingly competitive landscape.

• Interest Rates? Where are we now versus 12 months ago? What is new in the industry? What does it mean for the short-term rental market?
• How are you dealing with current market conditions?
• As the industry continues to consolidate how are owners and operators adjusting to market conditions and overall STR market performance?
• How are owners looking at acquisition and disposition activity in the year ahead? How can operators thrive in a consolidating industry?
• How is everyone navigating the ever-changing STR environment, from regulations to changes in OTA policies to changes in consumer preferences and behaviors?
• Which markets are hot? Which are not?

• How are mergers and acquisitions among property management companies reshaping the short-term rental landscape today and creating opportunities for growth and efficiency?
• Has the market become increasingly competitive? How have these consolidations allowed companies to expand their portfolios, streamline operations, and enhance service offerings?
• How do you make your first acquisition of a property management company, or, on the flip side, how do you position your company for a sale?
• What are some strategies for acquiring smaller (under 40 units) companies? How do you find them? How do you value them?
• Case studies & best practices for M&A

• Understanding Traditional real estate fundamentals and unique dynamics of hospitality operations
• Lending, investment, and property management underwriting strategies
• Assesing risks and regulatory challenges
• Pricing models

• What are some of the pros – and lesser-talked-about cons – of direct bookings? What is the ideal mix of business between direct and OTAs?
• How do you implement a direct booking strategy, and what does it look like?
• What are some different direct “tiers” you can offer?
• How much do you save/have you saved in commissions & fees compared to how much you spend on brand building, customer acquisition, website maintenance, booking engines, and the additional labor required to manage it all?
• What are the possible challenges/issues and how can you address them?
• New integrations worth noting?

• When do you know you’re ready to scale your STR portfolio?
• How do you grow from one property to 10? 10 to 50? 50 to 100+?
• What are the systems you need to have in place to be able to scale efficiently?
• What tools and technology will help to get you there? How should your team be structured?
• Things to be mindful of when scaling, timing? Proper management? Location diversity?

• Best practices for leveraging reach and visibility offered by social media platforms like Instagram and TikTok
• Are you maximizing the benefits of your social media channels and other brand marketing opportunities? What role does social media play in building brand recognition, driving direct traffic, and leading to brand loyalty and repeat bookings?
• Should you hire a dedicated social media manager or figure it out on your own?
• How are you using influencer marketing to build your brand and drive direct bookings?
• What’s your budget for influencer marketing? How do you determine the ROI? How do you vet potential influencer partnerships?
• What are some other best practices for maximizing the benefits of social media for your online STR presence?

By leveraging a franchise model, businesses can expand into new markets while maintaining operational consistency and brand integrity. How can STR operators use franchising as a method for scaling their businesses efficiently and expand into new regions without overextending resources? What are some of the benefits and challenges of turning your STR business into a franchise? How do you structure a franchise model that works for property management? What are some case studies of successful franchise expansion in the STR industry?

It’s a little-known but lucrative strategy that STR owners/operators should be making a lot more use of: how to leverage single and multi-family properties and boutique hotels to obtain government contracts for short-term housing needs for government workers. Learn everything you need to know about how to do it during this informative session.

• What are some foremost effective approaches to improve home owner acquisition?
• What are the most important things to highlight – Value? Support?
• How can property managers successfully use marketing materials to showcase success stories and profitability potential for homeowners? What about providing personalized consultations or hosting informational sessions?
• How can property managers establish credibility and build trust in order to successfully attract and retain homeowners in a competitive landscape?

• Are you an operator looking to gain some insight into best practices in short-term rental operations?
• Are you an owner seeking to better understand how operators operate? Join this AMA-style session where you can ask operators of all different sizes all the questions you have – ops, revenue management, growth, how to deal with negative guest experiences, how to deal with unruly owners, and more.

• What is new for property management software, channel managers, automated communication tools, dynamic pricing tools, maintenance management software, accounting software, data analytics tools?
• Why is developing your tech stack is absolutely essential to optimizing your operations business and enhancing efficiencies?
• How do all these different tools integrate? What can property managers do to make sure the tools they’re using are compatible? How many different tools are in your tech stack, and how can you streamline it?

• What advocacy of your business looks like in practice? Simple ways to get involved without overcommitting.
• The ROI of advocacy: How engagement can protect your investments and uncover new opportunities?
• Lessons learned: Strategies and tips from leaders who’ve made a tangible difference in their communities.
• What have you seen that has been implemented from an advocacy perspective that has been worthwhile and helpful to your properties?

• What is new in the interior design world that is resonating with those renting? Beautifully designed spaces, high-quality furnishings, thoughtfully curated decorative items, Instagrammable walls?
• Does higher investing in ID = Higher retention and interest in your STR?
• How have owners who have made such investments seen them pay off? What advice do you have for those who still need to be convinced? What are some case studies that demonstrate the ROI of interior design?

• How are you centralizing revenue data ? What property management software are you using?
• Dynamic pricing tools-What are the perks of using?
• Organization-wide simplification of rev mgmt
• What processes are automated vs. manual ? AI angle of this?

• What is involved in designing a unique, aesthetically pleasing property? Location ? Specific items?
• How can you create a hospitality experience that is truly “experiential”? How do you brand and market these kinds of unique one-off properties and micro-resorts?
• How are these properties standing out from the crowd of countless other vacation destination lodging options?
• What are some of the unique challenges of owning/operating such unique properties? How much should you invest to design, develop, build (or renovate) such a property?
• With higher upfront costs and higher operating expenses, how does the ROI of such properties compare to mid-tier properties (i.e., what’s the incentive for owners/investors)? What are some of the offerings to consider, from physical amenities to on-site programming?

• How is AI being used effectively in short-term rental operations? From enhancing the guest experience to optimizing dynamic pricing, the applications for AI in STR operations really are game-changing. How can AI enhance the guest experience through automated responses, chatbots, and predictive assistance?
• Can it be leveraged to optimize pricing based on demand, seasonality, and local events? How can AI be used in predictive maintenance so that maintenance is preventative instead of reactive, and avoid costly repairs? In what ways can AI-powered smart home devices be used to improve security and guest comfort?
• What kind of AI tools can be used for targeted marketing campaigns to improve occupancy rates?
• AI Updates in the past 12 months, how are we using it today in this industry?

• What are some of the opportunities stemming from regulations? How can fair and good regulations can help the short-term rental industry continue to be successful in the long term?
• Different rules for different municipalities?
• How are owners addressing regulatory challenges, and how is it impacting acquisition and/or exit strategies?
• How are operators navigating the ever-changing regulatory environment that varies by city and state and by property type?
• How are you making sure you are in compliance across your portfolio? How have they made adaptations to existing regulations and planning for new ones?
• In cities with highly restrictive regulations, how have STRs been impacted and how operators have adapted? Do we anticipate more markets will outlaw short-term rentals entirely?

What’s the “secret sauce” of top-performing companies, especially in this competitive environment? Let’s discuss specific examples and leave with actionable takeaways.

So much of the work of operating short-term rentals comes down to the unglamorous business of bedding et.al. Social media marketing is “sexy;” replacing mattresses is not. And yet, much of the work that operators do is dirty work. So, let’s talk dirty (work)! How often do you change out the mattresses? What about laundering decorative linens (such as duvet covers or European pillow shams)? What are the pros and the pitfalls of allowing pets? How often do you need to replace carpet/rugs/other textiles due to pet accidents, and is the ROI worth it? How do you manage laundry? If you're doing laundry in-house, what are your best practices? If you're outsourcing, what are you outsourcing and why? Have you considered starting a laundry facility (or already have one), and what are the economics of doing so?

• Medium- or mid-term rentals (MTR) are growing in popularity as a strategic alternative to the traditional short-term or long-term rental model. How can investors and property managers optimize for mid-term stays?
• How should operators adjust pricing strategies and occupancy management for MTRs?
• What are the regulations and operational nuances of managing MTRs? How can you identify the right markets where mid-term rentals can thrive?
• Should specific changes be standard across STRs transitioning to MTRs?

Screening and safety are paramount in the short-term rental industry, ensuring a secure environment for both hosts and guests. Effective screening processes - including thorough background checks, identity verification, and fraud prevention measures - help mitigate risks associated with property damage and bad guest behavior. Additionally, implementing safety measures - such as smoke detectors, secure entry systems, and clear emergency protocols - enhances guest confidence and satisfaction. What are STR operators doing to protect the properties they manage (and the owners’ investments)? How can rigorous screening and safety measures also cultivate a reputation for reliability, and attract more discerning travelers in a competitive market?

• What makes a really good property listing?
• What are the key elements that make one listing stand out above the rest?
• What are guests caring about in today’s market and how do you capture their attention, drive bookings, and even create brand recognition and loyalty?