In the bustling heart of Orlando, Florida, the Vacation Rental Management Association (VRMA) International Conference became a nexus for property management professionals, executives, and owners eager to delve into the industry’s latest trends and insights. During the conference there were breakout sessions and one of the most popular one was At the heart of this vibrant gathering was Nick Halverson, the dynamic CEO of Osa Property Management. Nick found himself on the stage as a distinguished panelist in a session that promised riveting narratives and invaluable lessons – “Tales from the Trenches: Crazy Stories and Lessons Learned.”

This exclusive panel, moderated by Brise Carpenter from Hostfully, featured other industry luminaries, including Moira Sedgwick of ‘A Chalet Collective’ and Jodie Cleer of ‘I Love Vacations.’ The event drew an enthusiastic crowd of over 125 people, with standing room only, primarily composed of property management company executives and owners eager to glean wisdom from the experiences of these seasoned professionals.

Brise Carpenter, a respected figure in the vacation rental industry, VP of Customer Success at Hostfully, took the stage as the moderator for this high-profile panel. With his wealth of experience, Brise expertly guided the discussion, ensuring that the audience was treated to a balanced and insightful exploration of the panelists’ experiences. His skillful moderation set the stage for an engaging session that promised not only to entertain but also to educate.

The Panel

The Panel was comprised of Nick Halverson, the CEO of Osa Property Management, , Moira Sedgwick, owner of ‘A Chalet Collective,’ and Jodie Cleer, owner of ‘I Love Vacations,’. Collectively they shared their unique perspectives and stories with everyone in the room. Each panelist represented a different facet of the vacation rental industry, making for a rich and diverse discussion.

Nick Halverson’s Journey – Tales from the Trenches:

Nick Halverson, with his characteristic blend of charisma and experience, regaled the audience with tales from the trenches of property management in Costa Rica. From navigating unexpected challenges (snake encounters), to celebrating triumphs (supporting local organizations during emergencies), Nick offered a transparent and candid account of his 15 year journey of managing vacation rentals in Costa Rica. His anecdotes ranged from the comical to the poignant, creating a connection with the audience as they saw the human side of property management.

Moira Sedgwick’s ‘A Chalet Collective’:

Moira Sedgwick, the owner of ‘A Chalet Collective,’ shared her insights into the unique challenges of managing chalet-style properties. Her tales resonated with those managing vacation rentals in niche markets, illustrating that, regardless of property type, the industry shared common threads of perseverance and innovation.

Jodie Cleer’s ‘I Love Vacations’:

Jodie Cleer, owner of ‘I Love Vacations,’ brought a different flavor to the panel, highlighting the importance of customer-centric approaches in vacation rental management. Her stories emphasized the pivotal role of customer satisfaction in building a successful property management business.

Audience Engagement and Lessons Learned:

The standing-room-only audience was not just passive observers; they actively engaged with the panelists, posing questions and seeking advice. The dynamic interaction between the panel and the audience created an atmosphere of shared learning, where insights flowed freely in both directions.

Key Takeaways for Property Management Professionals:

  1. Adaptability is Key: The panelists emphasized the need for adaptability in an industry that is constantly evolving. From technological advancements to changing customer expectations, property managers must be nimble and ready to pivot.
  2. The Human Touch Matters: Amidst discussions about technology and innovation, the panelists underscored the enduring importance of the human touch in property management. Building relationships with guests, understanding their needs, and providing personalized experiences remain foundational to success.
  3. Turning Challenges into Opportunities: Each panelist shared instances where challenges became opportunities for growth. From unforeseen property issues to unexpected market shifts, the panelists demonstrated resilience in the face of adversity.
  4. Community Collaboration: The importance of collaboration within the vacation rental community emerged as a recurring theme. By sharing experiences and lessons learned, property managers can collectively elevate the industry and navigate challenges more effectively.


It was an honor to have Osa Property Management represented on the panel. As the CEO of Osa Property Management, his journey, along with those of fellow panelists Moira Sedgwick and Jodie Cleer, offered a treasure trove of insights for property management professionals. Moderated by the adept Brise Carpenter, the session titled “Tales from the Trenches: Crazy Stories and Lessons Learned” provided an unforgettable experience for the packed audience in Orlando, leaving them inspired, informed, and ready to tackle the challenges of the dynamic vacation rental landscape.