Protecting Your Timeshare Legacy Through Smart Planning and Wise Partnership

Rising insurance costs, labor shortages, updated building requirements, and unpredictable weather patterns have placed new demands on already over-tasked operations. At the same time, vacation trends are shifting, with some owners using their timeshares less frequently and younger families exploring other travel options.

These factors have triggered serious conversations by many resorts about rightsizing to better match owner usage. By reducing the total number of units or operational footprint to mirror current owner usage and funding realities, a timeshare resort can add years of vacations. Other resorts boards are exploring full repurposing options, transforming all their timeshare inventory into whole-ownership condominiums, vacation rentals, multi-family apartments, or even alternative uses such as senior housing or wellness centers.

Resorts That Plan Ahead Protect Owners’ Investments

It’s important to note that not all self-managed legacy resorts are struggling. Many self-managed resorts are thriving. Guided by dedicated boards, healthy reserves, and involved owners, these resorts deliver great experiences to their guests and owners. These properties illustrate that timeshares can and do flourish with support from a well-versed board, thoughtful planning, transparency, and collaboration. They prove self-management can still be a winning formula.

After years of dedicated volunteer service, an increasing number of boards are choosing to step back and partner with a professional management company to ease their ever-more complex workload. Gaining access to expanded resources, experienced staff, and broader market reach to strengthen rentals, and operations elevate the owner and guest experience. It’s a way for a board to stay engaged and provide oversight while enjoying a well-earned reprieve from daily duties.

Whether a resort is thriving or wrestling with change, the reality is the same: the marketplace rewards vigilance, adaptability, and proactive planning. Evaluating the pressures and possibilities that exist today helps every board make informed decisions that protect the resort’s future and the value it delivers to owners.

Your Warning System May Call

Can you hear it? That iconic voice of the robot from Lost in Space echoing in your head – ‘Danger, Will Robinson, danger!’ It’s more than just an iconic pop-culture catchphrase for us boomers. It’s the sound of an internal alarm, the mind’s way of flashing red lights when something isn’t right. We all have that inner warning system. Sometimes it’s serious, other times it’s playful, but its purpose is the same: to make us pause, pay attention, and act before it’s too late.

Many self-managed legacy timeshare resorts have a dedicated Board of Directors – owners who share a genuine commitment to preserving the resort’s character, financial health, and quality of service. These volunteer boards often carry significant responsibilities while working with limited staff and tight budgets, carefully weighing every decision to find the best interest of their community. Yet these very challenges can sometimes leave a resort vulnerable to outside interests – groups with misaligned or conflicting goals that may seek influence or control.

We all know the old adage: if it seems too good to be true, it probably is. External power grabs rarely begin with a loud announcement; instead, they unfold quietly, step by step. Often, the initial promise of a singular activity to quickly fix issues that took decades to accumulate should be viewed with skepticism. Such as if the first step comes in the form of ambitious promises to rent or sell unused, off-season, or shoulder-season weeks. Yet those promises should raise caution when they ignore the realities of the market – realities that many seasoned professionals have already struggled with. The fact that associations hold so many weeks is proof enough that legacy timeshares are difficult to sell. And when the promised rentals or sales fail to materialize, the company’s true intentions often come into focus, as those promises give way to proposals to purchase the weeks instead.

Because each unit typically carries a vote, even what appears to be a modest purchase can influence the future course of action. If an adverse stakeholder voting power grows, the next step may be to back candidates for the board who align with a rogue operator’s interests, but not the owners’ interests. If enough of these candidates win, the board may gradually shift to directors who approve decisions that benefit a company rather than the resort owners. Understanding the fiduciary role of a board member may be lost of those with ill intent.

It is not only loosely organized firms positioning themselves to assume control of timeshare resorts; disruptive and contentious groups of owners also emerge, creating instability within the association. While many may have benevolent intentions, the

disregardof the financial, legal, or sometimes common-sense requirements is rarely beneficial in the long run. These groups often leverage social media to rally grassroots support, presenting themselves as a movement to “take back” the resort. Many of these owners hold multiple weeks, using them to operate profitable side businesses through rentals, and then vote themselves onto the board. Once in control, they frequently challenge established management practices, dismiss the expertise of prior boards, and too often disregard the bylaws and governing documents, placing the association and its owners at risk. Longtime vacationers, once passive, become opportunistic and convinced they can manage the resort more effectively, though experience shows this is rarely the case.

The consequences for a self-managed resort can be serious. Once an unfriendly party has enough influence, it may be too late to take corrective action. Monitor social media sites for rogue owners attempting to stir up discontent. Carefully research any group making unrealistic sales or rental promises. Review online ratings and industry references to see how these companies are regarded not just by owners, but also by peers in the marketplace. A lack of credible online presence, rogue social media activity, or consistently poor ratings should raise immediate red flags. Pay attention to whether these groups are validly licensed and whether they operate under shifting business names or shell companies, as this can be a tactic to avoid accountability. Legitimate organizations, by contrast, will encourage transparency, openly share their track record, and provide boards with clear contracts, verifiable commitments, and operational practices that inspire confidence. The key difference is that credible partners seek long-term stability for the association, while opportunistic groups are driven by short-term gains at the owners’ expense.

When Is It a Helping Hand – and When Is It Not?

When a resort faces declining finances, deferred maintenance, property degradation, or a shrinking base of dues-paying owners, it may be time to seek the guidance of a specialty management company. These professionals can help evaluate the association’s options and craft a strategic plan that may include right-sizing, repositioning, restructuring, and sale of part, or all, of the property.

Handled with proper legal oversight and full transparency in the board’s deliberations, such a course of action can often represent the best outcome for most owners. Open dialogue is essential, and owners should be encouraged to ask thoughtful, even difficult, questions to ensure all perspectives are considered. At the same time, it is important to recognize that people, properties, and businesses naturally move through cycles of growth, maturity, and renewal. Reimagining a resort and adapting it to its best new use

is not always a desired outcome by all, but a forward-looking opportunity that can preserve value, enhance the property’s relevance, and provide meaningful returns to owners. With the right planning, repositioning a resort can create fresh experiences for families, strengthen the surrounding community, and protect owners from less favorable outcomes, such as neglect, declining usage, or reliance on costly timeshare exit companies. Ultimately, proactive planning and transparent decision making turn potential challenges into opportunities to preserve the resort’s legacy while creating pathways for new possibilities.

The Role of Strong Governance and Professional Support

One of the strongest defenses an association can have is a sound governance framework. Bylaws should be clear, up to date, and include safeguards against manipulation of elections or board composition. Yet many legacy resorts still operate under documents drafted more than 40 or 50 years ago. Modernizing these governing documents is often critical to keeping associations protected and resilient. Key updates may include setting limits on the number of proxies any individual can hold, requiring formal verification of proxy intent, and mandating owner approval for major contracts, especially those extending beyond a few years. Equally important are transparent, independent election procedures overseen by qualified inspectors, ensuring that control is not concentrated in the hands of a few but remains accountable to the entire ownership.

Every timeshare association should engage independent legal counsel and other qualified professionals to review governing documents, agreements and contracts for potential pitfalls that could jeopardize the association’s interests. Business terms such as pricing, service levels, or duration are properly the responsibility of the board to evaluate and decide. Legal terms, however, carry binding consequences that require the expertise of an attorney to ensure compliance, mitigate risk, and safeguard the association. While an attorney may serve as a member of the board, that does not mean they should act as the association’s counsel. In fact, doing so can create conflicts of interest and expose both the individual and the association to unnecessary risk. Boards should be cautious in this regard and rely on independent legal counsel whose sole duty is to protect the association and its owners. It bears repeating – your association must have its own attorney.

Managing Conflicts of Interest

Equally important is a robust conflict of interest policy. Every board member should complete an annual disclosure identifying any relationships or financial ties that could influence their decisions. When a conflict exists, the director must recuse themselves from related discussions and votes. Policies should prohibit board members from receiving gifts, favors, or compensation from vendors without full disclosure. Some states may even require board education, as was recently enacted in Florida. These measures not only safeguard the integrity of decision-making but also reinforce trust among owners, thereby reducing opportunities for a potentially hostile party to exploit insider relationships.

Securing Financial Stability

Financial stability is another critical layer of protection. Resorts with strong reserves and transparent, audited financials are far less vulnerable to takeover attempts. Keeping maintenance fees unrealistically low may seem appealing, but it often leads to deferred upkeep and declining quality. By setting fair, sustainable fees, boards protect the resort’s value, avoid large special assessments, and give owners confidence that their vacation home is being cared for. Strong financial planning also helps reduce the risk of owners turning to costly exit companies or walking away from their weeks. Annual independent audits, clear financial reporting to owners, and adherence to reserve funding plans send a clear signal that the board is competent and proactive.

Financially stressed associations are often targeted by outside entities, such as exit companies, that position themselves as a ‘rescue’ solution to desperate owners who just want to out of their timeshare. Educate owners regarding the risks of companies that claim they can ‘get you out of your timeshare.’ Don’t wait for the annual meeting – create opportunities for engagement throughout the year. Online town halls, small group discussions, and open forums allow owners to share their views, ask questions, and gain a clearer understanding of budgets and resort operations. These conversations may also help identify and encourage future board members. An informed ownership base is not only more supportive of the board’s efforts but also more compassionate and understanding of the challenges the association faces.

Engaging and Educating Owners

The importance of owner engagement is often underestimated. A disengaged ownership is far easier for an outside party to influence. Regular communication through newsletters, digital portals, and town hall meetings keeps owners informed and invested in the resort’s future. Education about voting rights, board responsibilities, and warning signs of hostile activity empowers owners to make informed choices during elections and discourages them from supporting candidates whose interests may not align with theirs. Resorts should ask themselves: “are our owners paying out of a sense of obligation or are they still using it they way it is intended?”

No defensive strategy is complete without the guidance of Independent Legal Counsel – an attorney who represents only the association and its owners, not the management company. Remember, the management company’s attorney is engaged to protect its interests, not those of the association or its owners. The association’s attorney ensures impartial advice, especially when reviewing management contracts, vendor agreements, or governing documents. Independent counsel can also help the board avoid undesirable contracts with difficult terms. Some contracts can trap the resort in unfavorable arrangements for years, making it difficult to terminate the management company if service declines or fees become excessive.

Monitoring for Warning Signs

Boards should track unit sales and be alert to patterns suggesting bulk purchases by a single buyer or related parties. Voting trends should be monitored for unusual shifts, such as sudden spikes in participation by previously inactive owners. Contracts should be reviewed periodically to ensure termination clauses allow for change if the management company fails to meet expectations or if the owners vote for a change in direction.

Protecting Board Members

Because disputes over control can lead to legal challenges, board members must also protect themselves personally. This includes maintaining comprehensive Directors and Officers (D&O) Insurance — without naming the management company as an additional insured — and ensuring indemnification provisions are clearly spelled out in the bylaws. Meeting minutes should be detailed enough to show that decisions were made with due diligence and in the owners’ best interests, providing a clear record in the event of a dispute.

Planning Takeaways

· Governance Structure – Update the declaration and bylaws and voting rules to block control manipulation.

· When seeking a management partner, issue a Request for Proposal (RFP) to make true apples-to-apples comparisons.

· Financial Stability – Maintain strong reserves whenever possible and transparent reporting.

· Owner Engagement – Foster informed, active participation in governance. Hold town halls in addition to annual meetings.

· Legal Protections – Engage independent legal counsel and avoid contract traps such as Evergreen Contracts.

· Monitoring – Social media, track unit sales, proxies, and voting to detect patterns early.

· Board Protection – Maintain D&O insurance and document decisions carefully.

Bottom Line

A resort rarely declines overnight, but slowly when boards are distracted, owners are disengaged, and safeguards are weak. With the right protections in place — including updated bylaws, active owner participation, financial stability, vigilant monitoring, and independent legal guidance — your board can preserve the independence, value, and legacy of your timeshare resort, ensuring it continues to benefit the community it was built for. Ultimately, board members wear many hats all summed up in one word, fiduciary. Make sure that all decisions are in the best interest of all stakeholders and not just those whose passion for your resort may cloud their judgement.

Jeff Ingram is the Senior Vice President of Real Estate Redevelopment for Lemonjuice Solutions. To learn more about our strategic management program and other services, please contact Jan Barrow at solutions@lemonjuice.biz.