Like many people, we stumbled into the world of short-term rentals almost by accident. What started as one project quickly turned into another, and before long we realized we had learned lessons that could save other hosts thousands of dollars and countless headaches.
Our first adventure was restoring a 1915 farmhouse on 90 acres in rural Wisconsin.
There were construction surprises, budget overruns, endless decisions, and plenty of moments when we wondered what we’d gotten ourselves into. Joan and her family even lived in the farmhouse during much of the renovation, giving her a front-row seat to everything that can go right—and wrong—when bringing an old property back to life.
When Red Dog Trails finally welcomed its first guests, we discovered something we hadn’t expected: we loved creating memorable experiences for people. Watching families reconnect around the fire pit, hikers explore the trails, and city dwellers unwind in the country was every bit as rewarding as the income the property generated.
It taught us how to market a property, delight guests, solve unexpected problems, and, just as importantly, when it was time to sell. (We’ll share that story—and why we walked away from a successful rental—in our book.)
Inspired by the classic Southern dogtrot home, Joan and her husband designed a ranch-style house with a private guest wing. Today, it continues to attract travelers looking for comfort, privacy, and a unique place to stay.
What began as a backyard office evolved into one of Joan’s most successful rentals. Building the ADU meant navigating permits, zoning challenges, and months of persistence, but today the Scandinavian-inspired Nordic Nest has become proof that a small property can produce big results.
Jean took a different path by transforming her primary residence into a luxury mountain retreat near Shenandoah National Park. Converting a home filled with years of family memories wasn’t always easy, but it showed firsthand that your existing home can become a successful short-term rental with the right planning.
Every property taught us valuable lessons. Every challenge made us stronger hosts. And every success reinforced one simple truth, there’s no single path to building a successful short-term rental business.
Over the years, friends, neighbors, and strangers kept asking the same questions.
Most books focused on theory.
Most online videos covered only one small piece of the puzzle.
We wanted to create the resource we wished we’d had when we started—a practical guide filled with real experiences, honest advice, checklists, and lessons learned from properties that actually existed.
Whether you’re dreaming about your first Airbnb, converting a home you already own, or wondering if an ADU makes sense, we’ve probably faced many of the same questions.
If you’ve ever wondered whether a short-term rental could fit into your life, you’re in the right place.
Whether your goal is earning extra income, preparing for retirement, making better use of a second home, or building a long-term business, we hope our experiences help you move forward with confidence.
Have a question about our book, properties, or co-hosting advice? Drop us a message below.
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