Hassle Free RE

Welcome to Hassle-Free RE! Today, Dave Menapace and Will Van Wickler sit down with guest Matt Welch—a former CPG sales leader who left his W-2 to scale a short-term rental portfolio and co-hosting company across Maine. Matt shares how he and his partners built an owner-first management model, why certain amenities (hot tubs, saunas) outperform in specific markets, and how they’re preparing to expa...

Welcome to Hassle-Free RE! Today, Dave Menapace and Will Van Wickler take a closer look at vacation rental design trends and uncover why not all upgrades and amenities actually boost your ROI. From flashy but impractical amenities to simple design tweaks that consistently improve guest satisfaction, they share what really works—and what often gets overlooked. Dave and Will discuss common misses in...

Welcome to Hassle-Free RE! Today, Dave Menapace and Will Van Wickler break down what it really takes to scale beyond 10 properties in the short-term rental business. From hidden costs to operational complexity, they reveal the challenges no one talks about and the mindset shifts required to build a sustainable, profitable business. Dave and Will discuss why scaling isn’t just about acquiring more...

Welcome to our latest episode! Today, Dave Menapace and Will Van Wickler tackle one of the most pressing issues in real estate and hospitality—the growing wave of short-term rental regulations. From Boston and Portland to vacation markets like Cape Cod and Bar Harbor, they break down how local governments are shaping the landscape and what it means for investors, operators, and homeowners. Dave an...

Welcome to our latest episode! Today, Dave Menapace and Will Van Wickler dive into one of the hottest debates in hospitality—Airbnb versus boutique hotels. With firsthand experience managing both luxury vacation rentals and boutique hotels across New England, they unpack the shifts in traveler behavior, the challenges of guest expectations, and the long-term opportunities for investors. Dave and W...

Welcome to our latest episode! Today, we’re joined by Jason Muth, Co-Founder and Director of Customer Experience at Prideaway Stays. Jason is a 31x Airbnb Superhost, 29x Vrbo Premier Host, and a full-time entrepreneur who transitioned from a corporate media career to scaling a successful short-term rental and co-hosting business. His story is filled with insights on intentional growth, hospitality...

Welcome to our latest episode! Today, Dave and Will dive into one of the most crucial aspects of business success—building and managing a high-performing team. They share lessons from their own experiences in hiring, training, and leading virtual assistants (VAs) and in-person teams. Whether you're struggling to delegate or looking to scale your business efficiently, this episode provides actionab...

Welcome to our latest episode! Today, Dave and Will dive into the transformative power of mindset retreats, real estate conferences, and networking at high-level masterminds. Both recently returned from separate but impactful events in Las Vegas—Dave from the Freedom Mastermind and Will from Keller Williams Family Reunion. They break down their biggest takeaways and why stepping out of your comfor...

Welcome to our latest episode! Today, we’re joined by Chris Petzy, Co-owner and CEO of Seacoast2Summit Vacation Rentals. Chris is a real estate investor, coach, Airbnb Superhost, and industry thought leader. With over five years in the short-term rental space and a decade of experience in streamlining business operations, Chris has built a reputation for leveraging modern-day technology and assemb...

Welcome to our latest episode! Today, we’re diving into the proposed short-term rental (STR) ordinance in Newry, Maine, a market that has remained largely unregulated—until now. This draft regulation aims to introduce new safety and operational standards for vacation rentals, impacting everything from occupancy limits to fire safety, parking, and trash control. With the town seeking to balance the...

Welcome to our latest episode! Today, we’re joined by Adrienne Green for an insightful discussion on systemizing real estate investing and achieving true time freedom. Adrienne is a seasoned investor and entrepreneur who transitioned from running a real estate team to building a location-independent lifestyle while managing a robust rental portfolio. Through strategic delegation, virtual assistant...

Welcome to our latest episode! Today, we’re joined by Jonathan Levitt, Co-Founder and President of No Worry Home, for an insightful discussion about proactive home maintenance. Jonathan, a former attorney and co-founder of Outside GC, has a rich background in entrepreneurship and professional services. Leveraging his expertise, Jonathan created No Worry Home, a service dedicated to providing preve...

Welcome to our latest episode! Today, we’re joined by Lucas Piper, the owner and founder of Five Star Vacation Home Rentals, for an in-depth conversation about his journey in the short-term rental (STR) industry. Lucas’s path began with transforming his own home into a vacation rental, which evolved into a thriving career combining his passions for travel, hospitality, and helping others. With a b...

Welcome to our latest episode! Today, we’re thrilled to have Bernie Cesareo, a seasoned short-term rental (STR) entrepreneur and founder of Eagle Stays, join us for an insightful discussion. Bernie is not only a dedicated Airbnb Superhost but also a co-host and specialized bookkeeper for other Superhosts. With a unique real estate journey spanning decades, Bernie transitioned from long-term rental...

Welcome to our latest episode, where Dave and Will take a deep dive into the challenges and triumphs of the 2024 real estate market while sharing insights into what lies ahead for 2025. Drawing from their experiences in real estate, STR property management, and consulting, they break down shifting buyer profiles, market timing strategies, and the importance of having the right team. In this episod...

Welcome to our latest episode, where Dave and Will are joined by Jess Lea, Director of Operations at The 5 Star Co-Host, to discuss the nuances of maintaining short-term rental properties effectively. With her extensive experience in managing operations and consulting, Jess offers invaluable insights into categorizing maintenance issues, optimizing team responses, and streamlining operations to en...

Welcome to our latest episode where Dave and Will discuss the unique dynamics of winter short-term rental markets and how to prepare for the upcoming season. Drawing on their expertise in STR property management, consulting, and real estate, they explore strategies for success in snowy destinations and share exciting updates, including Dave’s new venture into midterm rentals. In this episode, Dave...

Welcome to our latest episode where Dave and Will explore the thriving short-term rental market of Old Orchard Beach, Maine. Drawing from Dave’s extensive experience in property management and consulting, and Will’s expertise as New England’s top STR-focused real estate agent, they provide actionable strategies for navigating this timeless destination. In this episode, Dave and Will dive into the...

Welcome to our latest episode where Dave and Will delve into the strategies and insights that make Sunday River one of the most desirable short-term rental markets in New England. With Dave's expertise in property management and consulting and Will's extensive experience in real estate, this dynamic duo provides a comprehensive guide to thriving in this unique year-round destination. In this episo...

Welcome to our latest episode featuring Jordan Harboldt, Assistant Sales Manager at Mainely Tubs and a 20-year veteran in the pool and spa industry. Jordan shares his extensive experience helping property owners enhance guest experiences with high-quality hot tubs, saunas, and swim spas. From selecting durable, energy-efficient hot tubs to the wellness benefits of saunas and versatility of swim sp...

In this episode of Hassle-Free RE, hosts Dave Menapace and Will Van Wickler dive into the world of real estate investment, focusing on the nuances of flipping properties versus undertaking new construction projects. They bring real-life insights on how each path presents unique challenges, potential pitfalls, and opportunities for success. Dave and Will discuss their own experiences, including les...

In this episode of Hassle-Free RE , Dave Menapace and Will Van Wickler tackle two important topics: managing guest reviews on platforms like Airbnb and VRBO, and finding the perfect time and strategies for buying a short-term rental (STR) property. Whether you're an experienced STR host or new to the business, understanding the nuances of guest reviews and the optimal buying times can significantl...

In this episode of Hassle-Free RE, Dave Menapace and Will Van Wickler dive into the key elements of creating the perfect offer when buying a home. Whether you’re a seasoned real estate investor or a first-time buyer, understanding how to craft an offer that stands out can be the difference between securing your dream property or losing out to another buyer. Dave and Will share insights from their...

Welcome to our latest episode featuring Kenneth 'Kenny' Bedwell, Founder and CEO of STR Insights, and host of the Cash Flow Positive Podcast. In this episode, Kenny dives into the world of short-term rental data and shares his journey from purchasing his first STR to founding STR Insights, a data-driven tool designed to help investors identify profitable markets. With 6 STRs across New York, Kenny...

Welcome to Hassle-Free RE! In this episode, Dave Menapace and Will Van Wickler tackle a crucial topic for short-term rental hosts: breaking away from reliance on OTAs (Online Travel Agencies) like Airbnb and VRBO. They dive into effective strategies for transitioning guests to direct bookings, helping hosts build stronger, more profitable relationships with their guests. Dave and Will share both s...