The Big-Ticket Retirement Buys That Deserve a Second Look (and Maybe a Pause)

A few years ago, I sat across from a couple—early 60s, newly retired, both looking the part of calm confidence. They had good pensions, low debt, and a solid financial plan in place. But somewhere between “we feel ready” and “we want to celebrate,” they’d landed on an idea: buy a vacation home near the coast.

I asked what made them so certain it was the right time.

Their answer was honest and familiar: “We’ve worked hard. It’s what we’ve always imagined retirement would look like.”

Here’s the thing: They could afford it. But “can” and “should” don’t always travel together in retirement. The home came with property taxes, insurance, upkeep, and an unfamiliar market. After we ran the numbers and looked at how it might impact their flexibility—travel, healthcare, estate planning—they pressed pause. And a year later, they thanked me. Not because they didn’t eventually buy something, but because they made the decision with clear eyes, not celebratory autopilot.

Retirement is full of big emotional shifts, and that often leads to big financial moves. Some of them are smart. Others? Worth a second look. This article isn’t about saying don’t spend. It’s about asking: Is this expense adding to your freedom, or quietly taking it away?

Takeaways

• Retirement can bring on a “reward reflex”—the urge to spend more than planned in the name of celebration or freedom.
• Big purchases like second homes, RVs, and remodels often carry hidden costs—insurance, maintenance, tax implications—that stretch far into the future.
• The right time to make a major purchase isn’t always right after retiring. Give yourself time to recalibrate your lifestyle and spending patterns first.
• Cash flow, liquidity, and lifestyle flexibility are more important in retirement than accumulating more stuff or square footage.
• “Affording” something doesn’t mean it aligns with your long-term values or needs—smart retirees pause to ask why, not just how.

Retirement Spending: A Mindset Shift, Not a Shopping Spree

Here’s something most people don’t realize until they’re in it: retirement isn’t just a phase—it’s a recalibration of identity. For decades, we’ve been trained to earn, save, and delay gratification. When the paycheck stops, it’s easy to feel like you finally have permission to spend more freely. And in some cases, you do.

But with that freedom comes new constraints—fixed income, longevity risk, and the need to keep liquid assets intact. The question becomes less about “can I afford this today?” and more about “will this limit me later?”

According to the Bureau of Labor Statistics, the average household led by someone 65 or older spends approximately $5,000 per month, and housing, transportation, and healthcare remain the top three expenses. Big-ticket purchases often affect at least one (if not all) of those categories.

1. The Second Home That Might Become a Full-Time Expense

On the surface, buying a second home in retirement sounds idyllic. A lakeside cabin. A warm-weather getaway. A place to host grandkids. It checks a lot of emotional boxes.

But here’s what often gets overlooked: A second property isn’t just a second set of keys. It’s a second set of bills. Property taxes, insurance, HOA fees, utilities, travel costs, and routine maintenance don’t go away when you’re not there.

And unless you plan to rent it out consistently, the costs can quietly eat into your retirement flexibility. Even those who do rent often underestimate the management workload or overestimate occupancy rates.

One client I worked with bought a ski chalet with dreams of family gatherings. It sat empty most of the year. After factoring in snow removal, heating bills, and seasonal upkeep, it cost them $20,000 annually—even without a mortgage.

Rent before you buy. Spend a full season in the area to test the lifestyle. And revisit your numbers in terms of net impact on liquidity and travel freedom—not just your monthly income.

2. The Dream Remodel That Turns Into a Money Pit

You’ve got the time. You want to finally renovate the kitchen, redo the bathrooms, or add that outdoor living space. Understandable. After all, you’re planning to be home more—and enjoy it. But renovations often cost 30% to 50% more than estimated, especially when older homes or “while we’re at it” syndrome enter the picture. Retirees, in particular, may be tempted to do all the upgrades at once—because, well, now’s the time, right?

The issue? Major remodels can tie up cash in an illiquid asset (your home), reduce flexibility to relocate, and rarely offer the return on investment that real estate websites suggest.

That $85,000 kitchen overhaul might make you happy, but it could also reduce your ability to fund long-term care needs or help a family member financially down the road.

A smart check-in: Will this remodel improve function, comfort, and safety, or is it mostly about aesthetics? Projects that support aging-in-place (like walk-in showers, better lighting, or wider doorways) are often more worth the spend than granite upgrades.

3. The RV or Boat That Becomes a Financial Anchor

Ah, the call of the open road—or open water. RVs and boats represent freedom, exploration, and a kind of American dream many retirees carry with them. And for some, it’s a lifestyle choice that pays off emotionally.

But these purchases are rarely financially neutral. Beyond the upfront cost (often six figures for quality models), there are fuel, insurance, storage, maintenance, and depreciation costs that add up quickly.

As soon as an RV leaves the dealership, it can lose around 20% of its value. Boats tend to depreciate more gradually—expect a 10–15% drop after the first year and up to 40% by year ten.

If you're not planning to use it consistently—or don’t enjoy the logistics involved—you may find yourself resenting the cost more than relishing the freedom.

Renting or joining fractional ownership programs allows you to try out the lifestyle first. Some retirees even prefer long-term Airbnb or RV share platforms rather than owning outright.

4. Helping Adult Children Financially—Without a Clear Plan

This one’s delicate. Many retirees want to be generous with their grown kids—whether it’s a down payment, college funds for grandkids, or help during a rough patch. It’s noble and understandable.

But I’ve seen this go sideways too many times when retirees act quickly and emotionally, without fully mapping out the ripple effects. Gifting or co-signing large amounts can compromise your own financial safety net, especially if you're drawing from tax-advantaged accounts to do so.

And there’s often an emotional cost, too. Generosity without boundaries can lead to resentment, expectations, or family tension.

Set a giving threshold each year that fits within your withdrawal rate. Or create a family gifting plan that reflects your values and financial capacity—possibly with the help of an advisor or estate attorney.

The IRS allows individuals to gift up to $18,000 per recipient (as of 2024) annually without triggering gift taxes. But just because you can doesn’t mean you should, especially if you're pulling from retirement accounts to do it.

5. Luxury Car Upgrades That Quietly Drain Capital

Maybe you’ve always wanted the convertible. Or the fully-loaded SUV with every possible feature. And now, in retirement, you feel like you've earned it.

But here’s the rub: cars continue to be one of the fastest-depreciating assets and luxury models are particularly expensive to insure, maintain, and repair—especially as they age.

Also, many retirees are driving less than ever, or find they no longer need multiple vehicles. I once reviewed a couple’s annual car-related costs and found they were spending over $15,000 annually for two high-end vehicles they barely used.

Consider leasing for short-term indulgences, car-sharing programs, or simply going pre-owned with certified warranties. Or, if you do go luxury, make sure it’s funded by discretionary spending—not from tax-advantaged retirement accounts that trigger income consequences.

Retire Like a Strategist, Not a Spender

The most financially confident retirees I’ve met didn’t get there by being frugal—they got there by being deliberate. They didn’t confuse freedom with automatic spending. They learned to pause, run the numbers, consider the long-term ripple effects, and, sometimes, wait a season before making the purchase.

Here’s the bigger idea: Retirement isn’t the time to stop dreaming—but it is the time to vet your dreams carefully. Some big purchases will absolutely be worth it. But others? They may be trying to fill a gap that presence, travel, volunteering, or connection could fill more meaningfully (and affordably).

So before you swipe the card or sign the dotted line, give yourself the gift of a second look.