Day one - Monday, February 1stMonday, February 1, 2027 - EST

• Where are we now versus in 2026? What is new in the industry? What does it mean for the short-term rental market?

• How are you dealing with current market conditions? Economic factors that are pressing.

• As the industry acquisitions continue, are owners and operators adjusting to market conditions and overall STR market performance?

• How are you looking at STR activity in the year ahead?

• How is everyone navigating the ever-changing STR environment, from regulations to changes in consumer preferences and behaviors?

• Which markets are hot? Which are not?

• Unique stories from the past 12 months if any?

• Labor market challenges and recruitment strategies

• What is the biggest hurdle you face in operating your STR properties?

• Compensation models: Per-clean vs. hourly, bonuses, benefits

• Quality control: Inspection protocols, checklists, photo documentation

• Training and onboarding: Standards, techniques, efficiency

• AI/Technology: What are you using to be more efficient in your operations?

• Scheduling and logistics optimization

• 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 AI/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?

• How does AI give you a competitive advantage?

• Owner/operator perspective vs. vendor viewpoint- what do you find most helpful?

• What types of unique STR properties are you managing and why? E.g. Treehouses, tiny homes, yurts, domes, shipping containers, historic, architectural etc

• Market demand: Airbnb Categories, Instagram culture, experience economy 

• Sourcing opportunities: Finding or creating unique properties 

• Development and conversion: Building or transforming properties 

• Permitting and zoning: Navigating regulations for unconventional structures 

• Design considerations: Balancing uniqueness with comfort and functionality 

• Pricing premium: 20-50%+ over comparable standard properties 

• Guest expectations: Managing expectations, educating guests 

• Operational considerations: Maintenance, accessibility, seasonality 

• Case studies in your portfolio

AI and data analytics are transforming the STR market, enabling predictive market analysis, automated underwriting (100 properties analyzed in time for one manual review), portfolio optimization, and 20-40% operational cost reductions. Leading firms deploy machine learning models analyzing billions of data points—property characteristics, transactions, demographics, satellite imagery, foot traffic, social media—generating insights impossible manually.

• 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?

• 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 ?

• 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 revenue management

• What processes are automated vs. manual ? AI angle of this?

• Portfolio Strategy: Managing pricing across multiple units with varying occupancy, amenities, and locations. How do you handle this?

• Tech Integration: Automating pricing and reporting with PMS and revenue management platforms. Any tools you are using?