R. Scott MacGregor, COO and Executive Vice President Lemonjuice Capital and Solutions
With the majority of U.S. timeshare resorts built before the turn of the millennium, aging infrastructure, outdated governing documents, and an evolving ownership base have created unique challenges for resort professionals and HOA boards. In a recent Resort Trades Learning Center interview, Sharon Scott Wilson, RRP, sat down with Scott MacGregor, Executive Vice President and COO of Lemonjuice Capital Solutions, to explore how timeshare professionals can approach these legacy properties with a fresh, sustainable lens.
As Scott puts it, “This is a remarkable and positive time of innovation and renewal in the timeshare industry.” But that optimism hinges on a willingness to plan proactively, engage owners thoughtfully, and rethink assumptions about property operations and governance.
MacGregor outlined a five-part evaluation model that any resort decision-maker—HOA board, management company, or individual owner—can use to assess and revitalize an older timeshare community.
Most boards begin with financials: cash flow, budgets, and maintenance fees. But sustainability today requires looking beyond next year’s budget to longer-term reserve planning. That means factoring in major infrastructure updates like plumbing, electrical, and mechanical systems—projects that weren’t always included in traditional reserve studies.
MacGregor emphasized that boards must move beyond the old paradigm of keeping fees artificially low. “If you’re not reinvesting properly, it catches up with you. This is no longer about refinishing the pool—it’s about replacing what’s behind the walls.”
Operational planning now includes more than staff scheduling or guest satisfaction metrics. It must account for succession—both for aging resort managers and HOA board members with institutional memory.
Technology also plays a growing role. From bandwidth capacity for guests to rental inventory distribution and electronic voting, technology can streamline operations and improve guest experiences.
One overlooked area? Accessibility. “We’re all getting older,” MacGregor noted, “and removing trip hazards, adding ramps, and simplifying access is vital—not just for ADA compliance, but for broader guest satisfaction.”
Many governing documents—CC&Rs, bylaws, declarations—are relics of a bygone era. They don’t accommodate digital voting, new communications standards, or evolving ownership structures. Updating these documents can pave the way for modern solutions, including:
Understanding who owns what is crucial—not just current owners, but the entire chain of title. This becomes especially important when owners vote on major changes or when association inventory is used as collateral for financing. In short: governance decisions and capital funding hinge on clean title data.
Perhaps the most overlooked—and most important—component is understanding what owners truly want. Surveys help, but often only engaged owners respond. The real insights lie in tracking down those who don’t respond—those who’ve fallen behind on maintenance fees or haven’t attended meetings in years.
By re-engaging disengaged owners, resorts not only build consensus but help protect vulnerable owners from scams, particularly from so-called “relief companies” that charge thousands to exit timeshares. “There are better options,” MacGregor said, “and they start with communication.”
Sustainable change doesn’t happen all at once. MacGregor advocates for a phased roadmap that starts with fact-finding—owner demographics, title records, physical condition, and governing documents—and then moves into planning.
“You don’t have to do everything in one year,” he advised. “But you must start somewhere.” Especially for properties approaching physical or financial obsolescence, early planning can mean the difference between recovery and collapse.
MacGregor also urged boards to extend their vision beyond annual budgets. A three-to-five-year capital plan can account for succession planning, inflation-adjusted reserve needs, and operational KPIs like rental income, owner retention, and online reviews.
Following recent natural disasters, including severe storms in Texas and Florida, Lemonjuice Capital Solutions has prioritized disaster planning. According to MacGregor, “It starts with a plan, and the plan starts now—not three days before landfall.”
Key elements of disaster preparedness include:
Post-disaster, MacGregor emphasized the importance of early physical assessments and insurance filings. “If everyone’s filing claims, you want to be at the front of the line—not the back.”
Owner communication is where all the planning converges. Lemonjuice uses a blended strategy: email, text, postal newsletters, Zoom town halls, and dynamic websites—including dedicated microsites for reimagination projects.
And while digital meetings are cost-effective, MacGregor encourages in-person events when possible. “People still crave connection—and there’s nothing wrong with making an annual meeting a fun gathering.”
Whether facing declining maintenance fee revenue, outdated utilities, or disengaged owners, every resort should begin with a question: Where are we now, and where do we want to be in three years?
Scott MacGregor’s advice is clear and actionable: “Start somewhere today. Begin fact-finding. Get the right professionals around the table. Your roadmap will write itself once you know the facts.”
For HOA boards, management companies, and timeshare professionals, the tools are available—and the time to act is now.
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For More Info: Contact Sharon@SharonINK.com or Scott.MacGregor@Lemonjuice.biz
Visit: LemonjuiceSolutions.com
This article is based on the July 2025 Resort Trades Learning Center interview with Scott MacGregor, hosted by Sharon Scott Wilson, RRP. Portions of this interview will appear in the September 2025 edition of Resort Trades magazine.
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