Too often, vacation rental maintenance programs struggle to turn a profit. From zero-dollar invoices to non-billable work orders, property managers often find themselves covering costs without seeing returns. But as the panelists in Breezeway’s ELEVATE 2025 session on “Maintenance Programs that Make Money” revealed, a well-structured maintenance program can do more than just keep properties in top shape—it can also drive revenue and minimize unnecessary expenses.
Featuring industry experts Adrien Shoemake (Kasa), Kris Ramsay (Pretty Picky Properties), Ben Wolff (Frias Properties), and moderator Tiffany Edwards (Coletta Consulting), this discussion explored practical strategies for building a profitable maintenance program while maintaining top-tier property care.
Below, we break down five key strategies to turn your vacation rental maintenance program into a revenue stream.
1. Eliminate the hidden costs of “free” maintenance
Many vacation rental operators fall into the trap of absorbing maintenance costs to keep owners happy. “It’s easy to just do small fixes here and there and not charge for them,” said Kris Ramsay. “But when you add it up, that’s thousands of dollars in lost revenue every year.” Instead of writing off these tasks, the panelists emphasized the importance of creating structured billing for maintenance services.
Ben Wolff shared how Frias Properties moved away from absorbing costs by implementing a transparent pricing model. “We developed a detailed fee structure so owners understand exactly what they’re paying for. This not only boosts revenue but also sets clear expectations.”
2. Set upfront expectations with owners about rates and fees
One common challenge in monetizing maintenance is getting property owners on board. According to Ben Wolff, the key is to be proactive and transparent. “How you're going to charge starts with the management agreement that you have with your clients. You have to outline everything very clearly in that management agreement and ensure that owners are aligned so that there are no surprises down the road.”
For example, Frias Properties has a monthly management fee, which includes weekly unoccupied security inspections and half an hour or less of guest-related maintenance. Beyond that, any maintenance will be billed at an hourly rate. Ben explains, “This shows owners what they're getting for their monthly management fee, and that we're not nickel and diming them for simple services like showing a guest how to work a TV.”
3. Improve operational efficiency
Maximizing your team’s time is critical to turning maintenance into a profit center. That means optimizing routes, reducing unnecessary trips, and prioritizing high-impact tasks.
The panelists agreed that wasted time and resources are a major drain on profitability. Kris Ramsay explained how Pretty Picky Properties optimized their workflow: “Most important for us is vendor coordination. We use Breezeway to schedule maintenance and prepare our properties for the summer season, which means the HVAC servicing, gutter cleaning, septic pumping, etc., and that way we’ve established relationships with those vendors should something pop up in the middle of the summertime. Plus, the relationships that we've developed with these vendors have enabled us to get the best cost for the owners, so the owners feel like they're getting a win.”
Ben Wolff agreed, “Breezeway is really good at giving our company operational data. So we ask our employees to use the templates that we've created in Breezeway, which have task tags loaded into them to determine if something's billable or non-billable.” This data allows them to evaluate the rate of billable work each employee is completing to stay on top of our finances and track tasks.
4. Leverage AI to troubleshoot issues with guests
Not every maintenance issue needs an in-person response. Sometimes, the fix is as simple as walking a guest through a reset button or showing them how to use a smart thermostat.
Kasa has implemented AI-powered chat tools that automatically suggest solutions to common problems. Adrien shared “We now can resolve 40% of guest issues in the moment with troubleshooting through AI. And for those that can't, we can go ahead and immediately assign a task out in the middle of the day so it's real-time feedback.” That 40% adds up over time, especially over hundreds of units.
Kasa also uses AI to scrape and categorize review data which proactively alerts them of any potential maintenance issues, like “the AC wasn’t working well” so that they can take action before it becomes a recurring issue. This type of automation not only reduces labor costs but improves the guest experience by resolving issues faster.
5. Actively communicate to build trust with owners
At Frias Properties, Ben Wolff shared that “what we always say is if an owner is going to be surprised by the billing on their statement, we should probably give them a heads up. If it's not asking permission, it's at least notifying them.” He explained that in their management agreement, they contractually don’t need owner approval for repairs under $500, but active communication before they get the bill goes a long way in building trust with homeowners.
Kris Ramsay expanded, “The ultimate goal is that owners trust you so much that they won't question some of the smaller fees, like buying caulking, batteries, or outdoor flood lights, because they know you. They trust that we're bettering the house, bettering the guest experience, and we're preventing more costly issues from popping up in the peak season.” In his experience, this trust and transparency helps retain homeowners for the long run.
Maintenance can drive both property care and cash flow
By shifting the mindset from maintenance as an expense to maintenance as a revenue driver, vacation rental operators can enhance their bottom line while improving property care. As these industry experts demonstrated, a strategic, well-executed maintenance program isn’t just possible—it’s profitable.
The key is recognizing the value your team provides—then making sure your pricing, processes, and reporting reflect that value. By eliminating “free” labor, setting clear expectations with owners, working efficiently, using smart tools, and communicating consistently, you can turn maintenance from a cost center into a competitive advantage.
As Tiffany Edwards put it, “You’re already doing the work. You just need to make sure you’re communicating it and getting paid for it.”
View all of the expert resources shared during ELEVATE 2025 and the full session recordings to continue elevating your property operations.
