In this episode of the Hospitable Hosts podcast, we’re joined by Natalie Painter, Broker at Preserve Realty Co. and Owner of Preserve Property Co., a boutique vacation rental management company in the Outer Banks, which is one of the most competitive and well-established vacation rental markets in the US.
Natalie is a property manager with 100+ properties and a Hospitable customer on the Mogul plan. Chatting with Miles, Natalie shares the biggest challenges she faced while growing her business and how automation and AI help her scale efficiently while maintaining a personalized guest experience.
Press Play now to discover how Natalie has built a thriving property management business and why software like Hospitable is crucial for hosts looking to grow while staying lean.
If you prefer to read the highlights, we’ve got a summary of the key takeaways below.
What Led Natalie to Start a Property Management Company
Natalie reveals she became passionate about real estate after she bought her first property on the Outer Banks 11 years ago. “Having that asset, having that investment, it can be so addicting. I think many Hospitable users understand that once you get one, it is something you like to build on,” she says. Natalie and her husband now have 12 investment properties, primarily short-term rentals. They also build beach houses in their area and then sell them. “That is one of the other cornerstones of our investment strategy.”
Navigating the Competitive Vacation Rental Market
Natalie points out that the Outer Banks is a highly competitive market dominated by big property management firms. However, it is one of the longest-established markets for short-term rentals, which suits her as a homeowner and real estate investor because all STR laws and regulations have been well-established.
Natalie underlines that she is involved in property management, from taking her clients “to the extra step of the way.” “I am in real estate sales through Preserve Realty Co. Navigating into property management is really to fill a gap I found in a traditional model system. So, we do have the tried and true vacation management companies, but it’s not for everyone. So, offering a tiered boutique luxury service is what I provide homeowners with, Preserve Property Co., a sister brand from my real estate company.”
“So when I sell somebody a house, I am driven by their goals and want to take them to the finish line, get them a successful property, and give them care and a personal touch. My property management caters to the experience of the homeowner and the experience of the renter, giving them a luxurious hands-on experience.”
Leveraging Technology, Automation, and AI
Managing 100+ properties is a lot of work, so Natalie uses Hospitable to streamline routine operations and takes advantage of its AI features. Hospitable’s solution for property managers helps Natalie efficiently manage all her properties, ensure a positive guest experience, and maintain a good work-life balance. “I’ve valued some of these integrations with Hospitable, taking some of the administrative burden away using AI.”
Natalie underlines that automation doesn’t replace personalization—it enhances it. It gives her time to focus on tasks that matter and offer personalized service. “That allows me to perform the duties I enjoy, which is just that whole guest experience, talking to my owners, knowing what’s going on.” Natalie thinks this is a “differentiating factor from a very large-scale property management company” that helps her stand out.
It’s also essential that using AI and automation in guest communication doesn’t make messages sound robotic. “Sometimes it is difficult not to get emotionally involved as well. So, say you have a guest needing a little more assistance. They’re having some questions and some difficulty. You’re working on a resolution. Being able to use AI to modify and graciously work through that issue is such a benefit, too. So I feel like there isn’t that robotic-ness to it, especially if you’ve built out your knowledge hub.”
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Advice for new STR Investors
Natalie shares her advice with individual investors who want to start renting their own houses and have chosen a competitive market. She thinks the most important thing to start on the best foot is finding a good real estate agent to help you purchase an investment property. Natalie recommends asking the agent for their credentials and finding out whether they have experience with vacation rentals.
“The skill to sell a house differs from an investment property. So I‘d say start there and get somebody with real estate investment experience, maybe personal experience in the industry. And then from there, that will be your knowledge hub to put all the other pieces together for you.”
Natalie also points out that today’s vacation rental guests have high expectations—they want luxury amenities, seamless check-ins, and excellent customer service. “So cater to those guests, make sure you’re hitting those high levels of cleaning and communication, and know that guests are evolving, their expectations are evolving.”
Tune in to the full episode of the Hospitable Hosts podcast to get inspired by Natalie’s success story and hear her best advice for homeowners who want to self-manage their rental properties.
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