Over Reliance on Tech Puts Short Term Rental Success at Risk

Written by:

Rudi Davis

Date:

05 Sep 2025

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Katie Cline, host of hospitality podcast Suite Success, argues that over-automation is creating a dangerous disconnect between hosts and guests in the short-term rental market.

The Human Element in a Digital World

According to Cline, while automation tools promise efficiency, they often miss crucial opportunities for personalization that can make or break a guest’s experience. “Everyone loves an automated message,” Cline says, “but if somebody books my rental in Saratoga the weekend of the Belmont Stakes, my welcome message shouldn’t say ‘What brings you to town?’ because as the host, I should know what brings them to town that weekend.”

This disconnect between automated systems and guest context represents a broader industry challenge, Cline argues. As more hosts rely on technology to scale their operations, they risk losing the personal touch that distinguishes exceptional hospitality experiences from merely adequate ones.

The Hidden Cost of Automation

Cline highlights that current automation tools in the short-term rental space often fall short of delivering real value to guests. Many systems rely on generic messaging that fails to account for the specific context of a booking, leaving communications feeling impersonal. Automation also tends to produce one-size-fits-all recommendations that don’t consider individual guest profiles or preferences. Perhaps most importantly, when problems arise, these systems lack the ability to provide personalized solutions, creating frustration for both guests and property managers.

“When somebody says, ‘Can you give me some suggestions for places to eat,’ the places that I suggest should be different if I’m talking to someone who’s told me they’re hosting their bachelorette party versus someone who’s told me it’s a multi-generational stay with their newborn,” Cline explains.

Finding the Balance

Rather than suggesting that property managers abandon technology altogether, Cline argues for a hybrid approach that blends automation with a human touch. She explains that technology can be invaluable in preparing drafts and streamlining operations, but ultimately it takes a person to ensure the final communication is relevant and thoughtful. By reviewing and adjusting automated outputs, hosts can avoid the pitfalls of generic messaging while still benefiting from the efficiency tech provides.

This balanced strategy not only saves time but also enhances the guest experience. By maintaining efficiency while ensuring communication feels personal, hosts can strengthen their relationships with guests and foster trust. Over time, this approach helps create more resilient businesses that are better equipped to adapt to changing guest expectations and market conditions.

The Business Impact

According to Cline, this personal approach pays dividends when problems inevitably arise. “I’ve had all the problems that all real estate investors have at some point—septic backing up, massive bees nests by the door,” she says. “Because I’ve built the relationship with those people before, they’re much more forgiving of me, as opposed to if I hadn’t had any interactions with them.”

A New Framework for Success

Cline suggests hosts should:

1. Use technology as a foundation, not a complete solution
2. Review and customize automated messages
3. Segment guest communications based on stay purpose
4. Maintain personal oversight of guest interactions

Looking ahead, Cline believes the most successful operators will be those who effectively balance automation with authentic hospitality. “We need to be careful about overly automating things,” she cautions. “How can we use technology to empower the human hospitality element? I think that really goes a long way.”