STR Secrets From America's Cleanest Property Manager

This discussion brings together data-driven analysis and decades of operational experience to reveal what it really takes to succeed in Santa Fe's unique vacation rental market. Will Risbourg, owner of Two Casitas, joins as a leading voice in Santa Fe vacation rental management, with his company earning recognition as a top performer in AirDNA's 2025 property manager rankings.

"We've been around since 1998. It's a family business—my mom started it," Risbourg explains, highlighting the company's deep roots in Santa Fe's hospitality scene. His claim that "we were the first people in New Mexico to rent short-term rentals online" underscores Two Casitas' pioneering role in the market. Today, the company's influence is substantial, with Risbourg noting, "We control about 10% of the total STR market in Santa Fe."

Operational Excellence in Santa Fe Vacation Rental Management (2025)

Company Growth and Market Position

Two Casitas' journey from two properties in 1998 to over 100 listings in 2025 exemplifies sustainable growth in vacation rental property management. The company's expansion strategy relied heavily on organic growth rather than aggressive marketing campaigns. Before Risbourg joined in 2014, the business operated primarily through word-of-mouth referrals, starting with a realtor friend's suggestion to manage properties for others.

By 2014, Two Casitas had grown to approximately 40 properties, distinguishing itself from competitors who treated short-term rentals as secondary to their real estate businesses. The company's singular focus on vacation rentals allowed them to develop specialized expertise in guest experience and operational efficiency. Growth accelerated after hiring a specialist for new home onboarding, reaching around 90 properties before COVID-19 temporarily stalled expansion.

The post-pandemic recovery brought renewed growth, but always within the constraints of operational capacity. As of 2025, Two Casitas manages just over 100 properties, representing approximately 10% of Santa Fe's total STR market. This market share is significant considering the fragmented nature of the industry, where the vast majority consists of individual owner-operators.

Navigating Santa Fe's Unique Market Dynamics

Risbourg describes Santa Fe as a "Goldilocks market" for the vacation rental industry in 2025—not too big, not too small, but just right for sustainable operations. The city's tricultural heritage, blending Anglo, Native American, and Spanish influences, creates a unique destination that attracts affluent, retirement-age travelers seeking authentic experiences.

This demographic advantage provides resilience during economic downturns. "When the entire country goes down significantly 50%, we might go down 10 to 15 just because of the nature of our clientele," Risbourg notes, highlighting how Santa Fe's visitor profile insulates operators from severe market fluctuations.

However, managing properties in Santa Fe presents distinct challenges. The city's older building stock requires more maintenance than properties in newer markets. Construction methods aren't as tightly regulated as in other parts of the country, leading to ongoing maintenance needs. Additionally, navigating city permitting and historic review processes adds complexity to property management operations.

The market operates under a 1,000-permit cap for short-term rentals, creating both stability and growth limitations. This regulatory framework prevents market oversaturation while ensuring existing operators can maintain quality standards without facing unlimited competition.

Scaling Operations: Lessons from Two Casitas

The transition from family-run operation to professional property management company required strategic decisions about growth and capacity. Two Casitas' approach prioritizes operational excellence over rapid expansion, a philosophy that has proven crucial to maintaining their high standards.

"Most of our growth has been organic. Providing a great guest experience leads to good reviews, which attracts new homeowners, creating a positive cycle," Risbourg explains. This virtuous cycle depends on maintaining quality at every step, particularly in cleaning and maintenance operations.

The company's commitment to sustainable growth sometimes means turning down opportunities. "We've halted company growth and turned down amazing properties because our cleaning staff wasn't ready to take on more inventory," Risbourg admits. This discipline ensures that every property receives the same high level of service, protecting the company's reputation and guest satisfaction scores.

Internal systems evolved alongside growth, including the creation of specialized teams for different aspects of property management. Beyond the cleaning partnership, Two Casitas developed an internal inspection crew to handle property checks, outdoor maintenance, and quality assurance between guest stays.

Guest Experience and Review Strategies for 2025

Communication and Proactive Service

Two Casitas' approach to guest communication balances accessibility with respect for privacy. Using Breezeway for text-based communication, the team maintains open channels without overwhelming guests with messages. This measured approach allows them to address issues before they escalate into negative reviews.

"There's no great secret. It's really about actively communicating with every guest," Risbourg states, emphasizing the fundamental nature of good communication. The company's philosophy extends beyond mere problem-solving to creating positive experiences through thoughtful preparation. Properties are prepared with lights on and climate control running before guest arrival, creating an immediately welcoming environment.

The company's refund philosophy represents a crucial differentiator in their approach to guest satisfaction. "Letting the guest lead the conversation often results in gratitude and can turn situations around," Risbourg explains. This approach recognizes that refunds are emotional rather than purely financial transactions, and that flexibility often yields better long-term results than rigid policies.

Proactive service extends to property amenities and maintenance standards. Two Casitas maintains all property features to the highest standards, ensuring everything functions properly before guest arrival. This attention to detail prevents many common complaints and demonstrates care for the guest experience.

The Profitability of Five-Star Reviews

The relationship between review scores and business success creates what Risbourg calls a "feedback loop" in vacation rental property management. High ratings justify premium pricing for both nightly rates and cleaning fees, which in turn support the investment in quality that maintains those ratings. This economic model demonstrates how operational excellence directly translates to financial performance in the vacation rental industry.

The stakes for maintaining this cycle are high. As Jamie Lane observes, "If you can't provide 100% of the service your customers expect, you can't do it." This uncompromising standard means that growth must always align with the ability to deliver consistent quality across all properties.

Two Casitas' commitment to quality over quantity has proven financially sustainable in Santa Fe's market. By focusing on properties they're proud to manage and maintaining exceptional standards, they've created a premium positioning that attracts both high-quality properties and guests willing to pay for superior experiences.

Cleaning Standards and Vendor Partnerships

The Role of Cleaning in Santa Fe Vacation Rentals

In the hierarchy of vacation rental operations, Two Casitas places cleaning at the apex. Their 20-plus year partnership with Estella's Cleaning Services forms the foundation of their operational success and guest satisfaction scores. This relationship transcends typical vendor arrangements, representing a true strategic partnership.

Estella, the owner of the cleaning company, brings specialized expertise that goes beyond basic housekeeping. She understands the unique demands of short-term rental cleaning, including tight scheduling requirements, varying property layouts, and the need for consistent quality across diverse properties. Her team's work directly impacts guest first impressions and overall satisfaction.

"There are no shortcuts to having a great cleaning staff—you need people who are good at it and reliable," Risbourg emphasizes. This reality shapes every aspect of Two Casitas' operations, from growth decisions to pricing strategies. The company has tested other cleaning services as potential backups but found none that match Estella's standards and reliability.

The financial investment in premium cleaning services pays dividends through maintained review scores and justified premium pricing. Rather than viewing cleaning as a cost center, Two Casitas treats it as a crucial value driver that enables their entire business model.

Managing Vendor Risk and Succession Planning

The deep partnership between Two Casitas and Estella's Cleaning Services creates both strength and vulnerability. Recognizing this dynamic, both companies have developed strategies to ensure long-term stability and continuity.

"There's a level of codependence between our companies—we're her biggest client and major source of income, so she needs us as much as we need her," Risbourg acknowledges. This mutual dependence has fostered open communication about succession planning and business continuity.

The companies have integrated their operations to a degree that would facilitate transition if necessary. Two Casitas assists with linen storage and scheduling, creating operational overlap that provides both efficiency and risk mitigation. "We work incredibly closely, almost as if we're employees of each other," Risbourg notes, describing a relationship that goes beyond typical vendor arrangements.

Knowledge transfer represents another crucial element of risk management. After two decades of partnership, Two Casitas understands Estella's standards well enough to potentially train another company if needed. This institutional knowledge, combined with documented processes and integrated workflows, provides some insurance against disruption.

Technology, Automation, and Efficiency in 2025

Tech Stack and Automation Tools

Two Casitas' technology strategy in 2025 balances automation with the human touch that defines their service. Breezeway serves as the operational backbone, managing scheduling, checklists, and communication workflows. This platform enables coordination between cleaning crews, inspection teams, and property managers while maintaining accountability through detailed reporting.

"We use Breezeway, which is a great scheduling tool," Risbourg explains, while noting that competitors like Operto offer similar functionality. The key lies not in the specific platform but in how it's implemented to support operational excellence.

Pricing represents another area where technology plays a crucial role. Two Casitas uses Beyond Pricing for dynamic rate management, with Risbourg personally reviewing and adjusting prices weekly. "Our pricing is automated, and our tech stack is integrated, but scheduling still requires manual input," he notes, highlighting the balance between automation and human oversight.

The company's tech stack includes various integrated software solutions that communicate with each other, reducing manual data entry and potential errors. However, the team maintains that technology serves to enhance rather than replace human decision-making in critical areas.

Balancing Automation and Personalization

While automation streamlines many processes, Two Casitas recognizes the limitations of current technology in delivering personalized guest experiences. The company experiments with AI chatbots for handling frequently asked questions but remains skeptical about their readiness for full deployment.

"Chatbots only know what you feed them and can't answer specific questions about a property's layout," Risbourg observes. This limitation becomes particularly relevant in Santa Fe's diverse property portfolio, where each home has unique characteristics and quirks that guests often inquire about.

The internal inspection team exemplifies Two Casitas' hybrid approach to operations. While Breezeway automates checklist creation and reporting, human inspectors perform the actual property evaluations. Their rigorous checklist covers everything from HVAC functionality to Wi-Fi performance, ensuring properties meet standards that automated systems cannot yet evaluate.

Manual scheduling, despite the availability of automation tools, allows for nuanced decision-making about routing, team capacity, and property-specific needs. This human oversight ensures efficiency while maintaining the flexibility to handle special circumstances or urgent issues.

Challenges and Opportunities in Santa Fe's 2025 STR Market

Market Trends and Economic Context

Santa Fe's vacation rental market in 2025 reflects both the resilience and challenges of a mature destination. The market experienced significant growth during the 2021-2022 post-pandemic boom, followed by a normalization period in 2023-2024. As of 2025, occupancy rates have stabilized above pre-pandemic levels but below the exceptional highs of the stimulus period.

"Our clientele skews retired and wealthy, so we get good nightly rates and guests less affected by economic ups and downs," Risbourg explains. This demographic advantage provides buffer against economic volatility, with Santa Fe experiencing smaller downturns compared to markets dependent on budget-conscious travelers.

The city's "land of mañana" culture presents operational challenges, particularly in securing reliable maintenance contractors. This cultural characteristic, while part of Santa Fe's charm for visitors, can complicate property management operations when urgent repairs are needed.

Looking ahead, Two Casitas is exploring new marketing initiatives to recapture some of the demand from peak years. However, the company approaches growth opportunities cautiously, ensuring any expansion aligns with their operational capacity and quality standards.

Regulatory and Operational Hurdles

Santa Fe's regulatory environment in 2025 represents both stability and constraint for vacation rental operators. The 1,000-permit cap provides market protection for existing operators while limiting growth potential. This framework has reached what Risbourg describes as "equilibrium," though tensions with local residents persist.

Political challenges remain a constant consideration, with ongoing community debates about the impact of short-term rentals on housing availability and neighborhood character. Two Casitas navigates these waters carefully, maintaining positive community relations while advocating for reasonable regulations that allow responsible operators to thrive.

Operational challenges center on property maintenance and contractor availability. Santa Fe's older building stock requires more frequent repairs than properties in newer markets. The lack of standardized construction methods adds complexity to maintenance planning and execution.

The company's growth strategy anticipates eventually hiring on-staff maintenance professionals, which would address both the reliability issues with contractors and enable more proactive property care. Until reaching that scale, they continue working with a network of independent contractors while managing the inherent scheduling challenges.

Growth Advice for New Property Managers

For property managers looking to scale in 2025, Two Casitas' journey offers valuable lessons about sustainable growth. "You can't just grow for the sake of growth. You have to earn it by doing a great job and outperforming others in your market," Risbourg advises.

The path from managing 1-10 properties to 50 or more requires fundamental shifts in operations and mindset. Early-stage managers can handle many tasks manually, but scaling demands systematic approaches and technology adoption. However, the core principle remains constant: guest and homeowner satisfaction must drive every decision.

"If you care about the quality of your guests' stay and your homeowners' experience, and you put yourself in their shoes, you'll stand out," Risbourg emphasizes. This empathetic approach, combined with operational excellence, creates the organic growth that has sustained Two Casitas for over 25 years.

New managers should resist the temptation to accept every property or pursue rapid expansion without supporting infrastructure. Building relationships with reliable vendors, particularly cleaning services, should precede aggressive growth targets. The short-term sacrifice of turning down properties preserves long-term reputation and sustainable success.

As the vacation rental property management industry in Santa Fe continues evolving in 2025, the lessons from Two Casitas demonstrate that success comes not from revolutionary tactics but from consistent execution of fundamental principles. In a market where anyone can list a property online, professional managers differentiate themselves through reliability, quality, and genuine care for all stakeholders in the rental experience.