Tax Season’s Over. But Did You Miss the Hidden Cost in Your Healthcare?

By Derek Fitteron, CEO & Founder of Emry Health Concierge

As you close the books on another tax season, certain patterns start to emerge — line items that prompt questions, categories that deserve a second look. For many successful families, one of the most overlooked is healthcare spending. Often tucked between investment summaries and charitable contributions, these expenses might appear as a number on a spreadsheet, but they rarely reflect the full scope of what you’ve spent, or the time it’s cost you to manage it.

If you go out of network, work with specialists, have children in therapy, or support a spouse or parent through ongoing care, you’re likely spending tens of thousands out-of-pocket each year, and these are just a few examples. But the larger and often more disruptive cost is the time and stress it takes to stay on top of it all: reviewing bills, following up on reimbursements, appealing denials and navigating a system that’s become too complex for even the most organized among us.

Without expert help — someone proactively tracking expenses, filing claims, coordinating with insurance, and leveraging every available benefit — the burden quietly builds. And while missed opportunities for reimbursement add up, it’s the time cost that compounds most quickly. The average family spends more than 100 hours a year managing healthcare logistics. That’s time better spent with your family, your business, or your life, not spent filling out paperwork or on hold with your insurance carrier.

Many default to simply paying the bill and moving on, trading peace of mind for convenience. But over time, the cost is far greater than it appears.

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Why It Matters More Than You Think

Even the most financially organized families often underestimate the time, complexity, and quiet inefficiencies that come with managing healthcare. In fact, it’s not uncommon for high-performing professionals — those with trusted advisors, detailed spreadsheets, and annual planning rituals — to overlook thousands in eligible reimbursements simply because no one is responsible for the process.

The system isn’t intuitive. And it certainly isn’t automatic.

Out-of-network care is common in this demographic — concierge physicians, private therapists, specialist consults. But unless someone is proactively submitting those claims on your behalf, your insurer may have no record the care ever occurred, meaning significant reimbursements could be quietly left on the table.

Even when you do have reimbursement accounts like HSAs, FSAs, or HRAs, tapping into them requires paperwork, itemized bills and persistence, all of which take time most families don’t have. As a result, many end up paying out of pocket for qualified expenses, missing the very tax advantages those accounts were designed to deliver.

And then there’s the paperwork itself: the denials that go unchallenged, the errors that go unnoticed, the benefits that quietly expire unused. These aren't dramatic mistakes but they’re cumulative. Over time, they can lead to unnecessary spending, missed financial opportunities, and a lot of preventable frustration.

For families navigating chronic conditions, supporting multiple generations, or managing executive-level benefits, the stakes are even higher. More providers. More plans. More complexity. And often, no clear system for keeping it all straight.

This isn’t about whether you’re capable of managing it. It’s about whether it’s the best use of your time — and whether the system is working for you, or the other way around.

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When Healthcare Spending Might Be Tax-Deductible

For some families — especially those with significant out-of-pocket medical expenses — there may be a potential tax benefit. Under current IRS rules, qualified unreimbursed medical expenses that exceed 7.5% of your adjusted gross income (AGI) may be deductible if you itemize.

While this won’t apply to everyone, it’s worth discussing with your wealth manager or tax advisor. And if it does apply, having organized, well-documented records can make all the difference. That’s one of the hidden values of proactive healthcare management: not just saving time and money throughout the year, but giving your tax team what they need when April comes around.

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The Emry Difference: Less Stress, More Control

For families who already rely on trusted professionals — a wealth advisor, a CPA, an estate attorney — managing healthcare should be no different. It requires the same level of oversight, organization and proactive strategy. That’s where Emry Concierge Health Advocates fit in.

We serve as your healthcare point person — the expert who ensures every eligible claim is filed, every reimbursement opportunity is explored, and nothing falls through the cracks. From selecting the best possible plan for you and your family, reviewing medical bills to catching errors, coordinating with insurers, and managing your HSA, FSA, or HRA submissions, we take on the work that typically drains your time and attention.

The result? You don’t need to think about whether a claim was filed, whether you missed a benefit window, or whether an out-of-network bill could have been reimbursed. It’s handled — and handled well.

Our clients often go from spending over 100 hours a year managing healthcare to spending just a fraction of that time — often no more than it takes to show up for an appointment. In one real example, we helped a family recover over $40,000 and reclaim more than 100 hours of lost time. Behind the scenes, we’re building a clear, comprehensive picture of their healthcare spending. That visibility not only reduces day-to-day friction but supports smarter decisions when it comes to insurance planning, benefit selection and long-term financial strategy.

As you look ahead to the year beyond tax season, consider this: healthcare isn’t just a line item to reconcile in April — it’s a system that, when managed well, can protect your time, your resources, and your peace of mind all year long.

Interested? Talk to your trusted advisor about Emry Health Concierge today. We look forward to working with you.  

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Whether you’re managing wealth—or navigating your own healthcare costs—Emry Concierge can help. Let’s connect.