Updated on July 7, 2025
As short-term rental operators trek toward an increasingly complex future, balancing economic pressure, shifting guest expectations, and tightening regulations, the gear they bring along for the journey matters more than ever.
At the RR Summit: Trailblazing to 2030 on May 21, 2025, a panel of leading STR tech executives unpacked the digital tools, safety protocols, and strategic vendor partnerships redefining how hosts and property managers operate. Representing Breezeway, Hostfully, Proper Insurance, and Avalara, these veterans shared both hard truths and opportunities for staying agile in a fast-changing industry.
Watch the full recording inside the RR Network >
Embracing the software shift
“The ones who are doing the best are sort of embracing the change and learning to love it,” said Margot Schmorak, CEO and Co-Founder of Hostfully. She pointed to the growing adoption of AI, smarter integrations, and operators actively asking how to automate more parts of their business. “There were so many things that were impossible a year ago that are possible now,” she said.
That embrace of change is transforming everything from guest messaging to revenue management. Property management software like Hostfully is becoming a backend workhorse and a flexible platform that evolves with the operator.
Safety and service are differentiators
If there’s one area where guest expectations continue to rise, it’s safety and service quality.
According to Jeremy Gall, founder and CEO of Breezeway, these have become the differentiators for short-term rental businesses.
“This business has turned into more than just scheduling a cleaning or a turnover. This is preparing for a guest stay, being committed to hospitality service, and delivering on the guest experience,” Jeremy said. “And I think that commitment is what is the big disruption, which is forcing people to really think about how they get this work done, what are the tools they use to do it, and how can they do it more effectively.”
There is growing interest in professional standards and accountability, particularly around property preparation. Jeremy credited industry thought leaders like Justin Ford for pushing safety to the forefront but noted that true guest satisfaction comes from seamless operational execution and adapting to each unique stay.
Hidden risk: Amenities and insurance gaps
“Short-term rentals really feel to be in this amenities arms race,” said Nick Massey, Chief Sales Officer at Proper Insurance. Hosts continue to invest in amenities to stay competitive, but those features often come with risks.
One example of a risky amenity is hot tubs, which can spread Legionnaire’s Disease, Nick said.
Legionnaires’ disease affects roughly 6,000 people each year in the United States, according to the Occupational Safety and Health Administration. But that number may not reflect the whole reality. Health officials believe the case count is higher, as many infections go undiagnosed or unreported.
Cases have been steadily rising since the early 2000s, peaking in 2018, based on data from the Centers for Disease Control and Prevention. While reports dipped during the early days of the COVID-19 pandemic, they’ve been climbing again since 2021.
Half of people who contracted Legionnaires’ Disease while staying at a vacation rental property had also used a hot tub during their vacation, according to the CDC.
“Taking a mindset…with the operations side is making sure we’re cleaning these things, that we have the right notices, that we’re hitting our checklist,” Nick said.
And it’s not just about guest safety. Nick warned of a tightening insurance market that’s catching property managers off guard. As carriers raise rates and limit coverage, operators face new pressure to ensure their policies match their risks. Hosts could be left exposed without comprehensive liability coverage, especially coverage that extends off-property.
Tax tech and AI enforcement
Even the most hospitality-focused hosts need to pay attention to tax compliance, and in 2025, the stakes are higher than ever.
“There’s a noticeable uptick in local enforcement,” said Max Fountain, Sales Executive at Avalara. He described how jurisdictions use AI-powered enforcement tech to scrape listing sites and identify unregistered or non-compliant properties.
But there’s a silver lining: “We’re starting to see more and more states–because of this technology–exploring statewide frameworks for short-term rental regulation and taxation, which could create and help a lot with consistency,” Max said. “We all hate having the bad actor that’s down the road who isn’t following regulation…By creating more uniform policies and…leveraging things like AI to find these people, it’ll create a more even rule of the road for everybody to be able to be on the same exact page.”
For operators juggling multiple properties and jurisdictions, tax tools like Avalara’s automate remittance and track licensing changes. But Max advised operators to treat compliance as an ongoing operational habit, not a last-minute scramble.
Tools that scale with you
From compliance to operations, the tools designed for large property managers are now flexible enough for solo hosts and lean teams.
At Breezeway, Jeremy said they’ve been surprised by how operators are stretching their task management software beyond traditional uses, applying it to airport transfers, vendor oversight, and even team training.
“We didn’t totally anticipate how the system would flex to be able to handle other services that you offer,” Jeremy said.
It reflects the leaner teams many operators are running today and the need for tools that can do more with less.
People power
Even as software evolves, the heart of hospitality remains human.
“Future-proofing any business…is all about making sure you really invest in your team,” Margot said. “So that when you need them to change what they’re doing…they are already bought in.”
Hosts who invest in training, align their teams with the company’s vision, and stay adaptable are best equipped for what’s next.
Link between advocacy and compliance
Beyond day-to-day operations, the panelists urged operators to see compliance and advocacy as linked.
“Tax and regulatory compliance is a form of advocacy in itself,” Max said. “That kind of behavior demonstrates legitimacy,
Nick echoed that theme, sharing how Proper Insurance advises policymakers to write realistic host insurance requirements. Their direct involvement has helped shape more workable laws in states like Missouri and Minnesota.
Jeremy closed by reminding that good operations equal good neighbors, and good neighbors are the foundation of sustainable short-term rentals.
“Advocacy starts by just being a great, contributing member of your community,” he said. “Yeah, it’s compliance and following the rules, but it’s about being a great operator in your community.”
Think of technology as a trail guide. The right partnerships, software, and mindset can help operators climb higher, react faster, and build lasting businesses.
…
