Boomer beware: 5 big-ticket buys seniors regret in retirement — and what you can do to avoid making these mistakes

Boomer beware: 5 big-ticket buys seniors regret in retirement — and what you can do to avoid making these mistakes Moneywise Mon, September 7, 2026 at 8:05 PM GMT+9 10 min read JPM -0.94% Photo by PeopleImages / Shutterstock Moneywise and Yahoo Finance LLC may earn commission or revenue through links in the content below.

One surprise that often hits retirees in their first few years is that even without the costs of working and contributing to retirement accounts, they end up spending more than when they held down a job.

Some financial planners cite three retirement phases: Go-Go, Slow-Go and No-Go. In the Go-Go years, typically 65 to 75, many healthy, young retirees spend big to check lifelong dreams off their bucket list — and make big purchases they may end up later regretting.

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A study from AARP (1) found that there are five spending categories retirees tend to regret splurging on, which you should be mindful of if you're in (or approaching) retirement.

Here's what you should watch out for and what you can do to benefit your wallet instead.

For many, middle age is a time to drive sensible cars and SUVs that can handle the daily commute and carpool lane. But when retirement is on the horizon — and teen drivers are in the rearview mirror — you might decide the time is right for an upgrade to the car of your own teen dreams.

Unfortunately, the value of any car declines as soon as you drive it out of the dealership. And taking on monthly car payments can be tricky now that your income is probably lower than it was during employment. Not only that, but the costs of gas, maintenance and insurance are typically higher for luxury cars.

If you do decide to treat yourself to a fancy ride, you could save yourself a few bucks by shopping around for better insurance rates.

According to Experian data, the national average cost of car insurance is $2,290 annually, or $191 per month (2). But luxury and antique cars come with much steeper premiums, making it incredibly valuable to comparison shop for the best rate.

By using a comparison platform like Insurify, you can instantly view quotes from top-rated providers to ensure you aren't paying a hidden 'loyalty tax' to your current insurer.

Just answer a few basic questions and Insurify will show you the most affordable deals in as little as 3 minutes.

Not only is the process 100% free, but you could also save up to 15% by bundling your car and home insurance.

Whether you're tired of making do with cramped quarters or you're just done dealing with the frustrations of an outdated house, upsizing to your dream home holds plenty of appeal. Just add an extension here, a brand new kitchen there and your dream house starts to take shape.

The downside is how quickly the costs of all those home improvement projects can add up, which is not an ideal scenario when you're on a fixed income. If you're not careful, your dream house can turn into a money pit, leaving you more stressed than when you started.

However, for those who have plenty of cash for the upgrades — and are disciplined enough to stick to a budget — creating a dream house could be a viable option.

But making these upgrades can cost big, so if you are set on the dream house, you'll want to make sure you're saving money on other home expenses.

Homeowners insurance is an essential cost that can increase at any time, so it's always important to ensure you're not overpaying here. The average single-family homeowner already pays $2,370 in yearly premiums (3), but to make matters worse, 47% of policyholders saw their rates increase in the past year, according to a 2025 study by JD Power (4).

This is bad news for those who simply auto-renew with their current provider every year. In such a quickly shifting landscape, it can pay to take two minutes to shop around for better rates.

OfficialHomeInsurance.com makes it easy to ensure you have the best price available. The platform will quickly compile all the rates available to you, so you can skip the hassle of calling multiple providers for quotes.

Just fill out a few details and you could save an average of $482 a year — money you can put toward that dream home improvement project.

After decades of working and providing for your family, retirement offers an opportunity to kick back and enjoy a well-earned extended vacation. Many retirees purchase timeshare properties with those perks in mind — a guaranteed vacation spot to share with family and friends.

But the reality of timeshares is less than idyllic. Beyond the initial investment, you'll be shelling out cash for an annual maintenance fee, utilities and taxes — all of which can rapidly drain your retirement savings. And if you try to surrender your timeshare, you'll typically only get pennies on the dollar compared to what you originally paid.

If you want to enjoy more vacation time in retirement, you may find better value in staying at local hotels than buying into a timeshare.

A better way to spend that timeshare money is to invest it, so you can use the returns to fund those future vacations.

Rental properties have long been a proven source of steady, passive income for high-net-worth investors so it's no wonder that real estate accounts for nearly 25% of the typical family office portfolio. However, the time, effort and costs involved in managing and maintaining multiple properties prevent many from investing. So unless you're a hedge fund titan or an oil baron, you've been shut out of one of the most profitable corners of the market.

Mogul steps in to bridge the divide here. This real estate investment platform offers fractional ownership in blue-chip rental properties, which gives investors monthly rental income, real-time appreciation and tax benefits — without the need for a hefty down payment or 3 a.m. tenant calls.

Founded by former Goldman Sachs real estate investors, the team handpicks the top 1% of single-family rental homes nationwide for you. Simply put, you can invest in institutional-quality offerings for a fraction of the usual cost.

Each property undergoes a vetting process, requiring a minimum 12% return even in downside scenarios. Across the board, the platform features an average annual IRR of 18.8%. Their cash-on-cash yields, meanwhile, average between 10% and 12% annually. Offerings often sell out in under three hours, with investments typically ranging between $15,000 and $40,000 per property.

Every investment is secured by real assets, not dependent on the platform's viability. Each property is held in a standalone Propco LLC, so investors own the property — not the platform. Blockchain-based fractionalization adds a layer of safety, ensuring a permanent, verifiable record of each stake.

Getting started is a quick and easy process. You can sign up for an account and then browse available properties. Once you verify your information with their team, you can invest like a mogul in just a few clicks.

Time on your hands plus money in your bank account can equal trouble if you're not paying close attention. With the magic of the internet, just a few clicks a day can quickly deplete your accounts and even leave you with a mountain of debt — not to mention a pile of stuff you probably don't need.

Are you really going to use that exercise bike you saw in a pop-up ad? Specialty cleaning gadgets may look like miracle workers, but soap and a cloth often achieve the same results. And prepackaged meal kits may be convenient, but the meals you make yourself are probably healthier (and much cheaper).

If you find you struggle with impulse buying and don't always know where your money's going each month, a budgeting app could help you curb this spending.

Monarch Money's expense-tracking system makes managing your finances simple. The platform seamlessly connects all your accounts in one place, giving you a clear view of where you may be overspending.

By linking your credit card accounts, you can monitor your payment progress in real time, create specific goals to get out of debt and set limits to keep your spending in check.

And, for a limited time, you can get 50% off your first year with the code WISE50.

It's natural for parents to want to see their children succeed and sometimes that means helping them over a financial hurdle. Perhaps you want to pay off their student loans, buy them a car or gift them the down payment for a home.

But while well-timed financial gifts can be meaningful, too much financial assistance can leave you unprepared to face your own future. And if you opt to give them a loan — and don't get the money back — it can lead to family discord and financial regret.

That's why it can pay to speak with a professional financial advisor before making any decisions around significant amounts of money. If you have a portfolio of $250,000 or more, platforms like WiserAdvisor can connect you with vetted professionals who specialize in this kind of planning.

Simply answer a few questions about your savings, retirement timeline and overall investment portfolio.

From there, WiserAdvisor reviews its network to match you — for free — with up to three vetted, reputable advisors aligned with your specific needs.

You can then schedule no-obligation consultations with your matches to determine who is the best fit for your long-term goals.

WiserAdvisor is a matching service and does not provide financial advice directly. All matched advisors are third parties and specific financial results are not guaranteed.

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