Meet Betsy Modglin, the force behind Pine Manor Estates. After launching her first short-term rental in Gulfport, Mississippi, Betsy organically grew her business into a full-service property management company rooted in hospitality. With OwnerRez as the backbone of her operations, she combines her background in hospitality, guest experience, and marketing to create meaningful stays for guests across Southern Illinois and the Mississippi Gulf Coast.
Can you tell us a little bit about your history?
I grew up in Southern Illinois with an early interest in hospitality and tourism, though my career initially took me far from home. For 20 years, I worked in the casino industry, ultimately serving as Vice President of Casino Marketing and Player Development. My role centered on building loyalty among high-value guests by ensuring their accommodations and overall experience exceeded anything offered by competing properties.
In 2009, I transitioned out of the casino world and into online marketing, consulting with casinos and small businesses to help them evolve from traditional offline marketing into integrated digital strategies. Life took an unexpected turn in 2011 when my 24-year-old nephew was diagnosed with osteosarcoma, a rare and aggressive bone cancer. I returned to Southern Illinois to be with my family, leaving behind my home in Gulfport, Mississippi. As his condition worsened, I converted that property into a long-term rental so I could remain close to home. Just one year later, we lost my nephew.
Around the same time, my tenant in Gulfport stopped paying rent. After completing the eviction process, I returned to find the home I had rebuilt after Hurricane Katrina severely damaged by neglect. That moment became a turning point. Rather than walking away, I chose to rebuild, again. This time, I reimagined the property as a short-term rental. During an incredibly painful season, the renovation process became healing. I realized that even in my own grief, I could create spaces that offered comfort, beauty, and joy to others. That experience marked the beginning of my journey in the short-term rental industry; combining my background in guest experience, marketing, and hospitality with a deeper purpose: creating meaningful stays that help people relax, reconnect, and heal.
After launching your first short-term rental, how did your business grow?
After owning and operating my own short-term rentals for several years, I began managing additional properties for a single owner in 2018. What started as six homes has grown to fourteen in just six years. This year alone, I’ve added two more vacation rentals, bringing my managed short-term rental portfolio to eighteen properties. In addition to vacation rentals, I also oversee eight long-term rentals and two conference centers. What began organically has evolved into a full-scale property management operation rooted in hospitality, systems, and guest experience, and it continues to grow every year.
What did your professional career look like before entering the vacation rental industry?
I actually began my career in secondary education as a high school English teacher. From there, I pivoted into grant writing, which opened the door to becoming Director of a Small Business Center at a community college. That role eventually led me into tourism, where I served as Director of a Tourism and Convention Bureau. While in that position, I began working with casino developers, and that connection quickly turned into an opportunity in the casino industry. Over the next two decades, I built a career in casino marketing and player development, working across multiple states including Illinois, Indiana, Louisiana, Nevada, Michigan, and Mississippi. Each step along the way built on the last, blending education, business development, tourism, hospitality, and marketing, experience that ultimately laid the foundation for everything I do today in property management and short-term rentals.
Are you from the geographical area where your properties are located, or did you move there later?
I’m originally from Southern Illinois, which is where the majority of my properties are now located. However, I also own and operate properties on the Mississippi Gulf Coast, where I lived for six years prior to entering the short-term rental industry. Having firsthand experience living in both markets has given me a unique perspective on guest expectations, regional tourism, and what it takes to successfully operate in very different environments.
If later, is there something that drew you to that area?
I was a strong proponent of tourism in Southern Illinois long before it became the thriving destination it is today. With the bluffs of the Shawnee National Forest, the growth of the regional wineries, the abundance of state parks, and the genuine hospitality of the people who live there, I always believed in the area’s potential. I never doubted what it could become and it has grown into exactly the kind of destination I envisioned. Being part of that evolution has been incredibly rewarding.
What do you love the most about the vacation rental business?
What I love most is seeing guests truly happy and enjoying the experience we’ve created for them. There’s nothing more rewarding than welcoming repeat guests who continue to come back, and hearing them say that no one does it quite like we do. Knowing we’ve created a place where people feel comfortable, cared for, and excited to return is what makes this business so meaningful to me.
What do you dislike the most about it?
The most challenging part is that it’s not truly a “clock out” kind of business. Hospitality doesn’t operate on a 9-to-5 schedule, which means I’m almost always accessible. Whether it’s a late-night question or a weekend request, guest needs don’t wait. That said, it’s part of the responsibility that comes with creating exceptional experiences, and I wouldn’t trade that commitment for anything.
How do you use OwnerRez to manage your business?
OwnerRez truly runs the backbone of my operation. From initial guest communication to collecting payments, generating smart lock codes, and managing ongoing follow-ups throughout each stay, it handles it all in one centralized system. I remember the early days of doing everything manually, and even with just two properties, I quickly realized that wasn’t sustainable. The moment I discovered OwnerRez, I made the switch and I’m fairly certain I was one of their early adopters. It allowed me to scale efficiently while maintaining the high level of guest experience I’ve always prioritized. Simply put, it gave me back my time and provided the operational structure needed to grow with confidence.
What is the most useful feature OwnerRez offers?
It’s honestly hard to narrow it down to just one feature because OwnerRez offers so much. But if I had to summarize what’s most valuable, it’s the automation, combined with the ability to maintain customization and personalization for each guest. That balance is critical. It allows me to streamline operations at scale while still delivering a warm, thoughtful experience that doesn’t feel automated. For me, that’s the sweet spot: efficiency behind the scenes, personal connection out front.
Drawing from her local experience in both Southern Illinois and the Mississippi Gulf Coast, Betsy has found a way to successfully build strong operations in two outstanding markets. We look forward to continuing to support Betsy’s businesses as she builds on her hospitality background and sets a standard of excellence in the vacation rental industry.