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Avoiding the Timeshare Snare: A Boomer’s Guide

Avoiding the Timeshare Snare: A Boomer's Guide

Avoiding a snare trap in the sandAvoiding the Timeshare Snare: A Boomer’s Guide

For countless baby boomers, the idea of owning a timeshare has been tempting. Envisioning a vacation spot without the hassle of full ownership, dreaming of far-off escapes, and having a guaranteed vacation destination can be alluring.

Yet, many have discovered that timeshares might not be the paradise they were promised. Instead, they can morph into financial burdens that are hard to shake off. Let’s look closer at Avoiding the Timeshare Snare: A Boomers Guide.

According to an article from GOBankingRates, one of the major money traps for boomers is timeshare ownership. Dawn-Marie Joseph, founder and president of Estate Planning & Preservation, points out that “one of the major money traps for boomers is a timeshare. Timeshares come with annual dues each year that you’ll be required to pay. They are also very difficult to sell.”

Why Timeshares Appeal to Boomers

Why do so many baby boomers find themselves ensnared in the timeshare trap? While the allure of owning a vacation spot without the full ownership responsibilities is tempting, many are navigating the murky waters of used timeshares. A report from sheds some light on this issue, highlighting the attraction to the variety of resort locations, the concept of future vacation savings, and the forced commitment to take annual vacations. Yet, in the current real estate landscape, the reality of timeshare resales can be quite different.

The secondary market for timeshares is filled with challenges, from lowball offers to outright scams. Many boomers, swayed by persuasive sales presentations, are led to believe in the numerous benefits of timeshare ownership. However, when it comes to the actual experience, it often doesn’t align with the dream. A significant number of timeshare owners regret their decision and would not recommend the path they took. For a deeper dive into the complexities of the timeshare market, Finn Law Group’s article on The Murky Waters of Used Timeshares provides some valuable insights.

Affordable vacations in membershipVacation Presentations Designed to Appeal

The allure of timeshares for the boomer generation is multifaceted. Many find themselves drawn in by extensive, persuasive sales presentations that can span hours. These presentations are often meticulously crafted, blending a mix of enticing visuals of exotic locations with compelling narratives.

Sales representatives employ a combination of clever misrepresentations and high-pressure tactics, painting a picture of unparalleled vacation experiences. Boomers are led to believe in the numerous and consistent advantages of timeshare ownership: significant vacation savings in the long run, a guaranteed commitment to taking annual vacations, and access to a vast array of resort destinations spanning the globe.

The idea of having a ‘home away from home’ in a favorite vacation spot can be particularly enticing. However, the reality can be starkly different. When the time comes for these boomers to book their vacations, they often encounter hurdles. The benefits they imagined, like prime booking dates or specific desired locations, often prove elusive. Year after year, many find that the dream sold to them doesn’t align with their actual experience, leading to frustration and regret.

The Downsides of Timeshare Ownership

  1. Ever-Rising Maintenance Fees: One of the biggest complaints from timeshare owners is the ever-increasing maintenance fees. These fees can become a significant financial burden, especially for retirees on a fixed income.
  2. Difficulty in Booking Desired Vacation Spots: Those with newer, points-based timeshare ownership often face delays and confusion when trying to book their desired vacation destinations. The lack of transparency in the reservations system and changing points values can make it very challenging to get the vacation you want.
  3. Difficulty in Selling: Many timeshare owners who want to sell their timeshares find it nearly impossible to recoup their investment. The secondary marketplace for timeshares is filled with scams and lowball offers.
  4. Changing Family Needs: As families grow and change, the timeshare that once seemed perfect may no longer fit the family’s needs. Yet, the owner is still on the hook for the maintenance fees and other costs.

endless upgrades

The Perpetual Lure of Timeshare Upgrades

For countless timeshare owners, the journey begins with the allure of unmatched privileges and elite perks. They’re drawn in by the promise of exclusive access to prime vacation spots and unparalleled amenities. However, what many don’t anticipate is the relentless cycle of upgrades that timeshare developers have strategically embedded into the ownership experience. This meticulously designed sales process is not a one-time event but a series of strategically timed owner upgrades spread over the duration of ownership.

Venture into any online timeshare forum, like those on TripAdvisor, and it becomes evident how widespread this issue is. Owners from various backgrounds voice their discontent and share tales of disillusionment.

Many recount how they were initially captivated by the offerings, only to later discover that to fully reap the benefits they were sold on, they’d need to commit to another, often more expensive, upgrade. This relentless push for upgrades doesn’t just put a dent in their finances, pushing many beyond their comfort zones, but also prompts a critical question: If the original timeshare was as advantageous as it was portrayed, why the incessant push for more?

Furthermore, timeshare developers often dangle the carrot of trade-ins or other one-time incentives, painting them as golden opportunities. Yet, in reality, these often fall short of owner expectations, adding to their growing list of grievances. This continuous upgrade carousel, while profitable for the developers, has become a source of financial strain and skepticism for many owners. They’re left navigating a maze of upgrades, questioning the true value of their initial investment, and often regretting their decisions based on the experiences shared by their peers in the timeshare community

Navigating the Timeshare Snare

If you’re a boomer who’s considering buying a timeshare or already owns one, it’s essential to be aware of the potential pitfalls. Here are some steps you can take to ensure you are making a sound decision for your future vacations:

  1. Do Your Research: Before buying a timeshare, thoroughly research the company, the location, and the terms of the contract. Read reviews from other owners and consult with a lawyer familiar with timeshare contracts. This way you are able to make an informed purchase decision.
  2. Consider Alternatives: Instead of buying a timeshare right now, consider renting one using vacation rental platforms. You can then quietly try it without the long-term commitment.
  3. Seek Legal Advice: If you’re unhappy with your timeshare and want to get out of your contract, consult with a timeshare lawyer who specializes in timeshare cancellations. They can help you navigate the complex process and potentially save you a lot of money and stress.

couple making an informed decisionRecap: Making Informed Timeshare Decisions Together

Timeshares can indeed offer the allure of dream vacations, but they also come with long term financial obligations. For boomers considering timeshare vacations, it’s crucial to tread carefully. By taking the time to thoroughly research and understand the intricacies of timeshare ownership, you can navigate away from potential regrets.

Remember, an informed decision is the key to ensuring that your timeshare experience aligns with your expectations. With the right knowledge and resources at your disposal, you can make choices that not only protect your financial future but also enhance your vacation experiences.

This article is for informational purposes only and is not intended as legal advice. Opinions expressed herein are solely those and do not necessarily represent the views or opinions of any other party. So, before buying or selling timeshares, always make sure to consider all aspects in order to make an informed decision that aligns with your needs and expectations.


Led by timeshare attorneys J. Andrew Meyer and Michael D. Finn with over 75 years of combined legal experience. The Finn Law Group is a consumer protection firm that specializes in Timeshare Law. If you need assistance with a timeshare related matter, contact us for a free consultation at 855-FINN-LAW.

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