When John Sullivan moved to Tokyo for his spouse’s job in 2019, he faced a dilemma: sell his three profitable Airbnb properties in Colorado or find a way to manage them from 6,000 miles away. Five years later, Sullivan not only kept those properties but expanded to eight units generating over $400,000 in annual revenue—all while living overseas.
“Everyone thought I was crazy to try running short-term rentals remotely,” Sullivan told me during our video interview from his Tokyo apartment. “But with the right software stack, I actually spend less time managing my properties now than when I lived 20 minutes away from them.”
Sullivan’s success highlights a growing trend in the $115 billion short-term rental market: location independence. According to AirDNA, nearly 30% of Airbnb hosts now manage properties in different states or countries than where they reside, up from just 11% in 2019.
The key to this remote management revolution? A carefully curated set of digital tools that automate everything from pricing to guest communication.
“Software has completely transformed this business,” says Avery Johnson, analyst at vacation rental research firm Skift. “We’re seeing hosts run increasingly sophisticated operations with minimal staff thanks to automation.” Johnson estimates that the average professional host now uses between 5-7 specialized software tools.
For Sullivan, the cornerstone of his remote operation is dynamic pricing software. “PriceLabs revolutionized my business,” he explains. The platform automatically adjusts nightly rates based on local events, seasonal demand, and competitor pricing. “It increased my revenue by 22% the first year while saving me hours of manual price adjustments.”
Beyond pricing, property management systems (PMS) serve as the operational hub for remote hosts. Sullivan uses Hostaway, which centralizes reservations across multiple booking platforms, automates messaging, and coordinates cleaning schedules. “Having one dashboard that connects to Airbnb, Vrbo, and Booking.com means I’m not constantly switching between apps,” Sullivan says.
The Federal Reserve’s 2023 Digital Economy Report noted that vacation rental technology adoption accelerated significantly during the pandemic, with PMS usage among professional hosts rising 74% between 2020 and 2022.
For remote investors, guest communication presents a particular challenge across time zones. Sullivan relies on Hospitable (formerly Smartbnb) to manage this critical aspect. “It sends automated messages based on triggers—booking confirmation, check-in instructions, mid-stay check-ups, and checkout reminders,” he explains. “The messages sound natural and personalized, and guests actually rate my communication higher now than when I was handling it manually.”
The system even recognizes and flags messages that require human attention. “If a guest asks about early check-in or reports an issue, I get an alert and can respond personally, no matter what time it is in Colorado,” Sullivan adds.
Security concerns initially made Sullivan hesitant about remote management. His solution combines NoiseAware sensors that monitor decibel levels with Ring cameras covering exterior entrances. “I get alerts if noise exceeds certain thresholds, which has prevented party situations maybe three or four times,” he notes. “The cameras let me verify guest count and assist with lockbox issues without being invasive.”
For maintenance issues, Sullivan has assembled a virtual team using TaskRabbit and specialized platforms like Spruce, which connects hosts with local service providers. “When a guest reported a leaking faucet last winter, I had a plumber there within three hours, all coordinated from my phone while I was at dinner in Tokyo,” he recalls.
Financial management represents another critical component for remote operators. Sullivan uses Stessa to track income, expenses, and property performance. “It connects to my bank accounts and automatically categorizes transactions for tax purposes,” he explains. “I can instantly see which properties are performing best and what my actual cash flow looks like.”
The Wall Street Journal reported last year that approximately 42% of new short-term rental investors are using property management software from day one, compared to just 17% in 2018, reflecting the growing sophistication of the industry.
Despite the technology, Sullivan emphasizes that human relationships remain crucial. “I have a property manager who handles the physical aspects I can’t do remotely,” he says. “The software doesn’t replace people—it makes their jobs more efficient and lets them focus on high-value tasks instead of administrative busy work.”
Sullivan pays his property manager 10% of revenue, substantially less than the 25-30% typically charged by full-service management companies. “Because the software handles so much, the on-the-ground role is much more limited,” he explains.
This hybrid approach—combining targeted software with strategic human support—represents what Johnson at Skift calls “the future of professional hosting.” According to their research, hosts using this model typically achieve 15-20% higher profitability than those relying solely on traditional management.
The tools Sullivan uses aren’t free—his monthly technology stack costs approximately $350 across all properties—but he considers it an essential investment. “When you factor in the increased revenue from dynamic pricing alone, plus the time saved, the ROI is massive,” he says.
For those considering remote management, Sullivan recommends starting with properties that are already stabilized. “Get your systems working smoothly while you’re local before trying to manage remotely,” he advises. “And test your emergency protocols before you need them.”
As the short-term rental market continues to mature, the barriers to geographical freedom are diminishing. “Five years ago, being a successful host meant living near your properties,” notes Johnson. “Today, with the right technology and systems, your physical location is increasingly irrelevant.”
Sullivan’s experience offers a compelling blueprint for investors seeking both passive income and location independence. “I’m literally on the other side of the world from my investment properties,” he says. “Yet I have more control and better results than ever before.”
That reality represents a fundamental shift in real estate investing—one where software doesn’t just supplement traditional management but enables entirely new business models built on remote ownership and automated operations.
