Key Takeaways from Our Expert Webinar

What does it really take to outperform in today’s competitive short-term rental market?

That was the driving question behind our latest webinar, hosted by Darren Carter of Topkey, with expert guests Evan Kaplan and Pedro Zavallos from Summer OS. With years of real-world experience as operators and technologists, Pedro and Evan broke down the data-backed strategies that top-performing short-term rental operators use to scale smarter, maximize revenue, and build profitable portfolios.

If you missed it live, don’t worry. Here’s your full recap of the insights, tools, and tactics shared during the session.

Meet the Experts

• Evan Kaplan, Head of Sales at Summer OS — a real estate tech veteran focused on revenue growth and partnerships.
• Pedro Zavallos, Head of Customer Success at Summer OS — with deep experience in acquisitions, hospitality, and real estate asset management.

Together, they’ve helped grow vacation rental portfolios and developed a powerful toolset to solve some of the industry's most common operational challenges.

Why Top 10% Operators Outperform

Top performers don’t guess — they project, track, and adapt.

Pedro and Evan emphasized that outperforming operators take a fundamentally different approach. Instead of relying on gut instinct or generic market lists (“Top 10 vacation rental markets”), they use competitive data sets, revenue projections, and real-time analytics to drive every decision.

As Pedro put it: “The last thing you want in this space is a mediocre home. Mediocre homes don’t make money — especially in down markets.”

Step 1: Pick the Right Market and Validate It with Data

Summer OS shared a key rule of thumb: Look at the relationship between listing growth and revenue growth in a market.

If listings are growing faster than total revenue, that’s a red flag. But if revenue is outpacing listings — that’s a signal of durability and opportunity.

For example: In their analysis of the 30A market, Pedro showed how Summer OS uses filters like bedroom count, listing duration (e.g. 270+ days listed), and review volume to benchmark performance and uncover revenue potential.

Step 2: Build Competitive Sets to Project Revenue

The foundation of any high-performance strategy is an accurate revenue projection.

Instead of just reacting to pricing tools, Pedro and Evan recommended creating competitive sets of similar homes in your market — same size, similar amenities, targeting the same guest profile. This helps you set realistic revenue goals and know exactly what you’re aiming for each month.

At Summer OS, these projections are built into what they call a “term sheet,” which becomes your operating blueprint.

“If you’re managing a home and don’t know what it’s supposed to make, you’re flying blind.”

Step 3: Use Amenity Data to Optimize Listings

Revenue isn’t just about location. Top-performing homes tend to have thoughtful, experience-driven amenities.

Examples from the webinar included:

• Hot tub vs. hot tub experience - A covered hot tub on a back deck doesn’t cut it anymore. Add string lights, views, and ambiance to turn it into a photo-worthy experience.
• Fire pits that invite connection - Well-designed outdoor spaces are major revenue drivers, especially in nature-heavy markets like the Catskills or Blue Ridge Mountains.
• Game rooms, media rooms, or even pet amenities - Study your market’s top listings to identify what amenities set them apart, then consider how you can differentiate.

Pedro emphasized: “Find your edge, don’t just copy. Identify what’s missing in your market and fill the gap.”

Step 4: Track Actuals Against Projections (Weekly, Monthly, Annually)

Creating a projection isn’t enough. Top operators monitor whether they’re actually hitting their targets and adjust when they’re not.

Summer OS allows users to:

• Track performance against projections on a monthly or weekly basis
• Identify underperforming homes in a portfolio instantly
• Unpack the variance (e.g. owner stays, bad reviews, missed pricing windows)
• Reforecast revenue targets when needed

As Pedro put it: “Good asset management means you’re always 60–90 days ahead of performance.”

Whether you’re up or down, you need to know why.

Step 5: Don’t Forget the Expense Side — That’s Where Profit Lives

Darren from Topkey highlighted a critical (but often overlooked) insight: cutting expenses has a huge impact on profitability.

For example:

A 5% cut in expenses can be the equivalent of a 26% increase in revenue if your margins are around 16%.

Topkey helps property managers automate expense tracking, reduce leakage, and capture billable charges that often slip through the cracks. This ensures that as you scale revenue, you’re not losing money through poor financial operations.

The Tech Stack Behind Top Operators

During the session, the group demoed Summer OS, a full-cycle asset management platform built for STR operators. Key features include:

• Market and asset-level analytics
• Competitive set builder
• Revenue projection engine
• Real-time performance tracking
• Visibility into underperforming properties
• Integration with major PMS platforms

While not a sales pitch, the tool demonstrated how the right software can drive sharper, faster decisions — especially for operators with growing portfolios.

Final Thoughts: The Winning Formula

If there was one big takeaway from the webinar, it’s this:

Top-performing STR operators use data to drive every decision, from acquisitions to amenities to pricing to expense tracking.

They don’t leave things to chance. They don’t blindly follow market trends. And they don’t tolerate underperformance without investigating.

With tools like Summer OS and Topkey, operators can bring a new level of professionalism and profit-focus to vacation rental management.

Want to Learn More?

• Explore Summer OS: Visit summeros.com
• Automate Financial Operations with Topkey: Visit topkey.io
• 📖 Read Customer Stories: Discover how real customers are saving $20–80 per unit/month at topkey.io/customers

Stay tuned for more webinars packed with actionable insights for vacation rental pros. Until then, here’s to smarter operations and better results.