News & Updates

In Part One, we examined the financial and operational pressures that legacy timeshare HOAs face from deferred maintenance and insurance spikes to the limits of traditional bank lending. Now we’ll focus on how thoughtful planning, market awareness, and the right management approach can turn those pressures into opportunities.

Across the country, timeshare HOA boards are confronting an uncomfortable truth – aging buildings, new legal requirements, and a more demanding travel market require money, often more than an association has planned for. Owners want attractive, competitive resorts and stable maintenance fees. Storms, wildfires, and rising insurance costs don’t wait for budgets.

The landscape for legacy timeshare resorts is quickly changing. Across the country, self-managed resorts are navigating a mix of challenges and opportunities that would have been hard to imagine a decade ago. Rising insurance costs, labor shortages, updated building requirements, and unpredictable weather patterns have placed new demands on already over-tasked operations.

Richard Winkler’s story begins in Cranston, Rhode Island, where a strong work ethic took root early. At just 11 years old he was delivering newspapers, and at 16 he began working at a neighborhood grocery store. “I worked every job you can imagine - except cutting meat,” he says, smiling. “You needed to be in a different union for that.”

Lemonjuice Solutions has successfully secured over $855,000 in grant funding and loan forgiveness to support essential water infrastructure upgrades at Mountainside Resort at Stowe. This achievement ensures long-term regulatory compliance and positions the property for future operational sustainability, despite growing environmental and municipal challenges across Vermont.

Jeff Ingram never expected a summer job at a Kissimmee hotel to shape the course of his life. But more than four decades later, his journey through hotel operations, vacation rentals, and timeshare leadership has led him to a unique role - reimagining aging resorts across the country. Today, he serves as Senior Vice President of Real Estate Redevelopment at Lemonjuice Capital Solutions.

During in-depth conversations with timeshare HOA boards across the country, one theme has consistently emerged — the critical importance of understanding the nuanced needs of owners. As one long-termed board president aptly stated, "Owners reveal their desires both through their words but also, and sometimes even more loudly, by how they use their checkbooks."

Jan Barrow never set out to become a leader in the timeshare world—but her journey from hospitality’s front lines to the executive team at Lemonjuice Solutions reveals a career defined by grit, vision, and an unwavering commitment to people.

Digital inclusion is not just a technical consideration but a moral and legal obligation. Hospitality brands that fail to make their digital experiences accessible risk alienating potential guests and owners and exposing themselves to legal risk. By embracing inclusive design, resorts not only comply with regulations like the Americans with Disabilities Act (ADA) but also demonstrate a commitment to welcoming all guests.

For Scott MacGregor, a four-decade journey in the timeshare and hospitality industries began with an unexpected start in the culinary arts. During a recent interview with TimeSharing Today, MacGregor reflected on his career, recalling the people and pivotal moments that shaped his path.

Alex Krakovsky’s journey from a timeshare owner in Ocean City, Maryland, to the Chief Executive Officer of Lemonjuice Capital Solutions is a compelling story of curiosity, perseverance, and innovation. Through personal experiences and a keen eye for opportunity, Krakovsky transformed his understanding of timeshares into a career dedicated to revitalizing and reimagining legacy resorts for a sustainable future.

Cedar Village was built in the early 1970s. It was a thriving association at one time, but in later years, it faced the typical challenges of a declining and aging ownership base, resulting in decreasing annual revenues to support the complex. We tried various strategies to reinvigorate the complex, association, and ownership, but our results were limited and insufficient for long-term sustainability.