Scaling a vacation rental business isn’t just about adding more properties. It’s about building systems that support growth without creating chaos, choosing technology partners who deliver real results, and surrounding yourself with people who fill in your operational gaps. These aren’t just nice-to-haves—they’re the foundation of sustainable multi-market expansion.
At Streamline Summit 2025, three industry leaders shared their hard-won insights on strategic scaling. Koen Roelens built a 600-property portfolio across Florida by openly admitting he’s terrible at operations and hiring accordingly. Larry Hoffer from Z Point helps property managers use data to target the right properties before competitors do. And Mishan Andre runs luxury properties in Cabo using Streamline’s automation to free up time for actual growth. Together, they reveal what it really takes to scale beyond your first market.
This episode is sponsored by Streamline.
The Critical Inflection Point: When to Invest in Operations
“My focus has always been on growth, on unit counts. It still is today because I think it’s the quickest and best way to grow your company. But we came to a certain number of units, a certain size of a company, that you say ‘if I don’t really put processes in place now, I’m never gonna really scale.'”
Koen’s journey started in hotels during the post-9/11 downturn. With occupancy tanking and time suddenly abundant, he launched what would become a 600-unit vacation rental business spanning multiple Florida markets. But his success didn’t come from being a master operator; in fact, he freely admits operations aren’t his strength and never have been.
For Koen, the turning point came somewhere between 200 and 250 properties. That’s when he realized growth without operational excellence isn’t really growth at all—it’s churn. Properties come in the front door while problems push them out the back. He had to make a choice: either become someone he wasn’t, or find people who excelled where he struggled. He chose the latter, building a leadership team that could handle the operational complexity while he focused on what he did best: sales and business development.
This inflection point looks different for every property manager, but the principle remains the same. There comes a moment when your existing systems can’t support the next phase of growth. Missing that moment means either plateauing or creating operational chaos that undermines everything you’ve built. Recognizing it early gives you time to build the infrastructure you need before cracks become craters.
Strategic Market Entry: Why Starting from Zero Is the Hard Way
“I think there are two ways for an established company to go to another market. One is organic growth. You start from zero. I think it’s the most difficult way. It’s the most expensive way.”
When Koen expanded into the Sarasota-Bradenton-Tampa corridor, he didn’t start by signing one property at a time. Instead, he looked for either a 20-unit cluster within a short-term rental community or a small existing company to acquire. This approach gives you immediate market presence, local knowledge, and established relationships rather than building everything from scratch.
The acquisition strategy isn’t just about speed. It’s about buying credibility and operational infrastructure. When you acquire a local company, you’re not just getting properties—you’re getting people who understand that market’s nuances, existing vendor relationships, and operational workflows that already function. You inherit their reputation and their owner relationships rather than having to prove yourself property by property.
But acquisition brings its own challenges, particularly around culture integration. Koen’s approach here is equally strategic: hire hospitality-minded locals, then gradually align them with your company culture rather than forcing immediate wholesale changes. This measured approach respects what’s already working while steering the new team toward your standards over time. It’s about dialing things in, not blowing them up and starting over.
The Communication Foundation: What Makes Everything Else Work
“When I sit with an owner and they are interested in our product, it always comes to communication. Always. If you find the right communication, they will follow you. And it’s the same for the guests. If you communicate the right way in all shapes and forms, it’s no problem. Everything will fall in place.”
Across all the complexity of multi-market operations, Koen keeps coming back to one fundamental principle: communicate more than you think you need to. With owners, with guests, with your team—transparent, proactive communication smooths out problems before they escalate. It’s simple in concept but demands discipline in execution, especially as you scale.
This isn’t about sending more messages. It’s about ensuring the right information reaches the right people at the right time. When owners know what’s happening with their properties, they trust you. When guests receive clear information about their stay, they’re more forgiving of minor issues. And when your team knows expectations and has the information they need, they can solve problems without constant escalation.
Koen tells his employees to communicate, over-communicate, and then communicate some more. Everything else—owner retention, guest satisfaction, operational efficiency—flows from this foundation. It can feel overcomplicated when you’re in the weeds of day-to-day operations. But if you follow this rule consistently, the complexity starts to resolve itself.
Building Your Leadership Team: Hiring People Smarter Than You
“The people aspect is key to me. In the beginning I hired, fired, hired, fired, hired, fired. But at a certain point you gotta find the right people around you because you cannot do it all yourself. So as you grow, you gotta trust other people.”
Koen went through the typical hiring churn that most growing businesses experience. But eventually, he figured out what separated good hires from great ones: finding people who were not just competent, but actually better than him in their areas of responsibility. His current leadership team is young, focused, and motivated—and they come up with strategies he admits he never could have developed himself.
This requires genuine humility and trust. You have to empower people to make decisions, even when those decisions differ from what you might choose. You have to get comfortable with not being the smartest person in the room about operations, technology, or revenue management. Your role shifts from doing the work to creating the environment where the right people can do their best work.
The payoff is enormous. When you surround yourself with people who excel in areas where you’re weak, the whole operation elevates. They bring fresh perspectives, challenge your assumptions, and build systems you couldn’t have imagined. Koen describes it as letting the train run while he listens and tweaks where needed—but the train itself is powered by people who are better operators than he’ll ever be.
Data-Driven Growth: Finding the Right Properties Before Your Competitors
“We have every single residential property in the United States in our own platform. If you’re a property manager, you have access to every property record and we update it monthly. 125 million properties.”
Larry Hoffer’s company Z Point built Owner Point, a tool that fundamentally changes how property managers approach acquisition. Instead of randomly pursuing whatever properties come across your desk, you start with comprehensive data about every residential property—all 125 million of them nationwide. Then you layer on 15 different data sources to identify not just any properties in your market, but the right properties for your business model.
This means understanding mortgage balances, property values, whether homes are already listed on VRBO, and whether they’re owned by investors. Property managers can filter 8,000 potential properties down to 1,000 prime targets, then immediately access owner contact information and demographic profiles. The result is targeted marketing to owners most likely to sign, rather than shotgun approaches that waste time and budget.
The bigger insight here is that strategic scaling requires intentionality. Random growth might work early on, but as you expand into new markets, you need to know exactly which properties move your business forward. Data eliminates guesswork and helps you grow efficiently rather than just quickly. It’s the difference between adding any properties and adding properties that actually improve your portfolio quality and profitability.
The Vendor Relationship Strategy: Consistency Builds Credibility
“When you show up at a trade show the first time, people may notice you. They show up the second time, they’d say, ‘oh, they’re still in business.’ And over several years, they expect that you’re there. And you know, we’re credible.”
Larry’s insight about trade show ROI applies equally to property managers evaluating vendors. When vendors show up consistently year after year, it signals stability and commitment to the industry. They’re not flash-in-the-pan solutions that disappear after 18 months. They’re building relationships and proving they’ll be around when you need support.
This matters more than most property managers realize. Choosing technology partners isn’t just about features—it’s about partnership quality over time. Can you reach someone when things break? Will they integrate properly with your other tools? Do they actually understand vacation rental operations, or are they just selling generic software? Consistency in showing up, both at events and in ongoing support, answers these questions better than any sales pitch.
Larry’s company invests disproportionately in trade shows for their size because they know relationship ROI takes years to develop. The first touchpoint creates awareness. The second visit proves they’re still in business. By year three or four, their presence becomes expected and their credibility is established. Property managers should look for this same pattern when evaluating vendors—are they building relationships, or just hunting for quick deals?
Implementation Reality: The Learning Curve Is Real But Worth It
“In the beginning it was not the easiest. In the beginning it was compared to what we came from, it was clunky. It was just difficult from the perspective of getting into it and understanding where to go.”
Mishan Andre runs luxury properties in Cabo—we’re talking $15,000 per night and up—using Streamline as his property management system. But his relationship with the platform wasn’t exactly perfect from day one. Coming from their previous system, it felt overwhelming. With so many features, reports, and options, it took real effort to onboard properly and understand how everything worked together. After seven years with Streamline, he’s candid about the initial learning curve.
But here’s what matters: once they pushed through that implementation phase, the momentum became unstoppable. Streamline created genuine efficiency in their operations, optimized their business processes, and gave them freedom to focus on growth rather than constant firefighting. It required dedicating one team member—Skylar, their tech wizard—to really own the system and keep everything running smoothly. But now it operates like a locomotive that you can’t stop, with pieces and parts building on each other every single day.
The lesson here applies to any significant technology implementation. There will be a learning curve. Things will feel harder before they feel easier. But if you choose the right system and commit to learning it properly, the compounding benefits far outweigh the initial struggle. Mishan’s team now runs 30 to 40 automated triggers daily on their normal operating schedule, freeing them to work on business growth rather than manual task management.
Automation That Actually Works: Triggers That Compound Your Efficiency
“One of my favorite parts has to be the triggers. When something happens in our system, it creates an action somewhere else. We have something like 30 or 40 triggers a day on a normal operating schedule. The more that you can automate, the more it frees you up to go out and grow the company.”
Mishan’s favorite Streamline feature is the trigger system—automated workflows where one action sparks multiple others automatically. When a booking comes in, it might trigger owner notifications, guest communications, housekeeping assignments, and revenue updates simultaneously. These triggers handle routine operations automatically, freeing the team to focus on relationship-building and strategic initiatives.
Setting up these triggers required upfront work. Creating rules, testing workflows, and refining processes to ensure everything fired correctly took time and attention. But once those 30 to 40 daily triggers were established, they became invisible infrastructure—constantly working in the background to keep operations running smoothly without manual intervention.
This is where automation delivers its real value. It’s not about replacing human judgment for complex decisions. It’s about eliminating repetitive manual tasks that slow you down and create opportunities for errors. Every automated workflow gives back time that you can invest in owner relationships, guest experiences, market expansion, and strategic planning. The more you automate, the more capacity you create for the work that actually moves your business forward.
Why People Behind Technology Matter As Much As The Technology Itself
“I really appreciate how Streamline has worked well with other vendors we use. Not only do the technologies work well together, but the people work well together. So when we have an issue with our website or we have something that needs to be troubleshooted, the teams communicate effectively with each other and they’re able to figure it out.”
Mishan highlights something crucial that often gets overlooked in technology discussions: the people behind the platforms matter just as much as the features. When he has an issue that spans multiple systems—say, something involving both Streamline and BizCor, who built their website—the teams actually talk to each other and collaborate on solutions. There’s no finger-pointing or passing the buck. They just figure it out.
He describes his relationship with Siraj from Streamline as having a brother in arms. When problems arise, Siraj either fixes them immediately or takes ownership of finding the solution. Mishan often hears from other vendors like Inhabit, Lynnbrook, or RentalGuardian saying Siraj already called them and they’re working on it together. That proactive collaboration is invaluable when you’re focused on running properties, not troubleshooting technical integrations.
This is what separates good technology partnerships from great ones. Features matter, but so does having real humans you can reach who genuinely care about solving your problems. Mishan also gives a shout-out to Jennifer from Streamline, who helped them navigate trust accounting challenges as their company grew. These personal relationships—knowing people by name, having them show up consistently, feeling confident they’ll follow through—create the foundation for long-term success with any technology platform.
The Conference Strategy: Working On Your Business, Not Just In It
“I would say come to conferences. Come to conferences like [Streamline Summit]. Connect with other people. See how they are doing certain things. I always learn from these conferences. Take the time out of your business to work on your business, don’t be always in the weeds.”
Koen’s final piece of advice addresses something every growing property manager struggles with: finding time to step back and gain perspective. Conferences like Streamline Summit, VRMA, and industry investor events aren’t just networking opportunities—they’re strategic learning environments where you discover how other operators solve problems you’re currently facing.
The key insight is distinguishing between working in your business versus working on your business. When you’re in the weeds daily, you’re focused on immediate operations—responding to owner requests, handling guest issues, managing your team. That work is essential, but it doesn’t move you forward strategically. Working on your business means stepping back to evaluate systems, learn new approaches, and connect with peers who’ve already navigated the challenges you’re facing.
Conferences accelerate this learning dramatically. Instead of figuring everything out through trial and error, you can learn from others’ mistakes and successes. You discover new vendors, hear about emerging trends, and build relationships with people who understand your challenges because they’re living them, too. For scaling property managers, this external perspective becomes increasingly valuable as your operation grows more complex.
Scaling a vacation rental business across multiple markets demands more than just ambition. It requires recognizing when to invest in operations, hiring people who are better than you in critical areas, and choosing technology partners who show up consistently with real support. It means using data to grow strategically rather than randomly, and building systems that compound efficiency over time.
The property managers who scale successfully aren’t the ones who try to do everything themselves. They’re the ones who communicate obsessively, empower strong teams, invest in the right tools, and create time to work on their business instead of just in it. They attend conferences, learn from peers, and build vendor relationships based on trust and consistency. They recognize that sustainable growth comes from building infrastructure that supports expansion, not just signing more properties and hoping it all works out.
Whether you’re at 50 properties or 500, these principles apply. The specific tactics might change, but the fundamentals remain constant: people, processes, and partnerships done right create the foundation for everything else.
To hear the full conversation between Lynell, Koen, Mishan and Larry on The Vacation Rental Show, follow the links below: