Transforming Aging Timeshare Resorts with Strategic Management

Scott MacGregor’s Role and Vision

MacGregor described his role as ensuring seamless operations across Lemonjuice Solutions. "My official title is Executive Vice President and Chief Operating Officer," MacGregor began. "I focus on resort operations, delivering hospitality and management services to our association clients. I also work closely with our HR department because our people are the bedrock of our organization." He emphasized Lemonjuice’s commitment to fostering collaboration across departments to achieve positive project outcomes.

"Our business development team is critical in connecting with properties that need our services," MacGregor added. "We focus on building long-lasting relationships with resorts to help them thrive—not only in the short term but also in the future."

Jan Barrow’s Strategic Perspective

Barrow outlined her responsibilities in guiding resorts through the complex decisions they face.

"As Senior Vice President of Business Development, I work with HOA Boards of Directors to develop deliberate plans for legacy resorts that address their unique challenges," she explained. "These plans often involve strategic management, rentals, sales strategies, or innovative solutions that meet the ongoing evolving needs of owners and the marketplace."

Barrow highlighted Lemonjuice’s proactive role in promoting its services through industry publications and conferences. "We also collaborate with our marketing and PR teams to ensure resorts, and their owners, know we’re here to help," she said.

Challenges Facing Legacy Resorts in 2025

MacGregor identified several key challenges legacy resorts will face in 2025.

"Most of these properties are over 35 years old and will be forced to deal with aging infrastructure and owners. Rising property and casualty insurance costs are creating additional financial pressures," he said.

Florida resorts are grappling with new reserve requirements under the Condominium Safety Act. "This legislation mandates engineering studies and proper funding for structural repairs, placing a significant burden on budgets," MacGregor explained. He also cited labor market pressures as a major concern, noting the rising costs of wages and benefits.

The Impact of Severe Weather

Barrow expanded on the challenges posed by severe weather. "Intense, repetitive storms have devastated resorts and surrounding communities. Boards and staff often face the dual challenge of rebuilding the resort while recovering personally from their own losses," she said.

Navigating FEMA regulations, along with local and state requirements, combined with managing insurance claims, adds significant layers of complexity. "Conflicting requirements between agencies can delay reopening, further straining resorts’ financial and operational resources," Barrow noted.

Owner Communications and Strategic Management

Lemonjuice Solutions prioritizes clear communication with owners. "Beyond written communications and customer services, we also host town halls and create websites specifically designed to address owners’ questions about processes and provide regular updates," MacGregor said. He emphasized the importance of owner engagement, saying, "Giving owners a voice and options is critical to maintaining trust and participation."

Barrow elaborated on the company’s strategic management approach.

“We are a multi-disciplinary management company that offers strategic management services. We begin with a comprehensive evaluation of each property. This includes assessing financial performance, governance structures, market conditions, owner feedback through surveys and town halls, and the physical infrastructure to develop customized solutions,” she explained.

This comprehensive strategy has been applied to nearly 40 resorts under our Resorts Reimagined™ program. "Sometimes we find that partial reimaginations, such as combining timeshare and whole ownership units, can revitalize a property," Barrow added. Many of the properties we work with are thriving and have years of robust operations ahead—although nearly all have areas they'd like to enhance, whether in governance, accounting and finance, facilities management, or owner communications. Meanwhile, a smaller but increasing number of associations are encountering more pressing challenges. These require our specialized expertise in areas such as restructuring, title management, and financing solutions.

Facilities, Risk Management, and Financial Stability

MacGregor discussed Lemonjuice’s investment in facilities evaluation and risk management.

"We conduct full property evaluations to identify safety issues and prescribe necessary infrastructure improvements," he said. "We also work closely with our insurance partners to create holistic risk management profiles for each resort."

Financial management is another cornerstone of Lemonjuice’s approach. "We analyze cash flow, plan for future investments, and conduct ‘what-if’ scenarios to help boards make informed decisions," MacGregor explained. "Our goal is to ensure resorts can meet their financial obligations while providing excellent experiences for owners."

Reimagining Resorts

Barrow described the Resorts Reimagined program as a lifeline for struggling properties.

"For some resorts, market pressures and aging ownership bases make traditional operations unsustainable. In those cases, we guide boards through an orderly wind-down while maximizing value for owners," she said.

Barrow emphasized the importance of flexibility in these plans. "Every resort is unique, and our solutions must adapt to changing circumstances. This process involves multiple conversations with boards to ensure we’re aligned with their fiduciary responsibilities and goals," she explained.

Due Diligence and Transparency

Barrow stressed the importance of due diligence when boards consider their options. "Resorts need to research potential partners thoroughly, ask for references, and understand all fees involved," she advised. "Transparency and trust are critical in these relationships."

MacGregor added, "Our commitment to excellence is reflected in our membership to organizations like the American Resort Development Association. We take pride in delivering top-rated services that align with the best interests of resorts and their owners."

Success Stories

MacGregor and Barrow shared examples of Lemonjuice’s impact.

One success story involved Bay Club in Ocean City, Maryland. "Initially, the board believed the resort needed to shut down," Barrow recounted. "We implemented a partial reimagination, combining whole ownership condos with timeshare units. This approach stabilized the budget, allowing for significant renovations, and created a vibrant, modern mixed-use property."

Another example was Pinecrest Resort in Pigeon Forge, Tennessee.

"The resort was on the brink of bankruptcy when we stepped in," Barrow said. "We managed the property, facilitated an accelerated sunset of the timeshare, and sold the resort to a company specializing in military family vacations. Owners received unexpected payouts, and the property was revitalized for a new purpose."

About Lemonjuice Solutions

Lemonjuice Solutions is a leader in strategic management and reimagination for legacy timeshare resorts. With a team of industry experts and a proven track record, the company offers comprehensive solutions tailored to the unique needs of each property. From financial management and facilities evaluation to owner engagement and risk mitigation, Lemonjuice Solutions is committed to preserving the value of timeshare resorts and enhancing the vacation experience for owners. To learn more about Lemonjuice Solutions, please contact Jan at 863-602-8804.