Q4 2025 Newsletter
Elliott Vaughn • October 28, 2025
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Medicare Open Enrollment!

Retirement faces two lifelong financial threats:


The rising cost of living (taxes are included in this category!).
And the rising cost of healthcare.


Medicare is the shield against the second. But only if you actively maintain it.


If you are already on Medicare — or about to enroll — the most important truth you can internalize is that Medicare is not a “set it and forget it” decision. It is a living system that is revised every year, and those revisions can materially change what you pay, which medications are covered affordably, and which physicians will continue to care for you. Standing still in a system that is constantly moving is the most predictable way to lose ground.


Original Medicare paired with a Medigap supplement — most notably Plan G — continues to provide the broadest access to care and the most reliable protection against large and unpredictable medical expenses. Clients fortunate enough to hold this combination and continue to afford the premiums generally should remain right where they are, because it represents what millions of retirees later wish they had kept.


Where the greatest financial surprises (especially this year) likely occur in Part D drug coverage. A plan that seemed irrelevant last year because you rarely filled prescriptions can suddenly become painfully expensive simply because formularies shifted or your preferred pharmacy is no longer “preferred.”


Spending just a short amount of time on Medicare.gov each year to verify drug and pharmacy pricing can provide savings that meaningfully support your long-term financial independence.


For more complex medication needs, HeyMoe.com can assist in locating lower-cost alternatives and manufacturer programs, and SHIP.org offers unbiased guidance from state-appointed counselors. Harbor Wealth has no affiliation with these organizations — our only interest is protecting you from preventable expense.


Medicare Advantage plans are heavily advertised as low-cost, all-in-one solutions, yet the low upfront premium can often obscure the potential for higher, harder-to-control costs later. Provider networks can contract without warning, prior authorizations can become barriers to care, and those who later try to return to Original Medicare may be required to medically qualify for a new Medigap policy. Too many retirees learn that last fact only after it is too late and all of us at Harbor Wealth want you to avoid that.


Premiums rise, copays move, drug coverage reshuffles, and the rules evolve — all annually. None of it arrives with fanfare or a helpful nudge from Washington. Like your Social Security timing decision, these changes are yours alone to stay ahead of.


Open Enrollment ends December 7. After that, decisions effectively lock in for another year, for better or worse.


PLEASE KNOW! Clients of Harbor Wealth do not need to navigate this alone. We maintain relationships with independent Medicare brokers whose sole purpose is to help you evaluate your current coverage and ensure that it remains aligned with your health needs and retirement plan. Their guidance comes at no cost, and their advocacy can help you avoid the silent erosion of both financial peace and access to care .But this help is only useful if it is called upon in time. Please please please, do not wait until the final days before December 7 to act.

If you or someone you love would benefit from a Medicare review before December 7, reach out to us. You have built a lifetime of financial security — and we intend to help you keep it.

12 Potential Tax-Savings Opportunities in O.B.B.A

On July 4th Congress passed the “One Big Beautiful Bill Act” (OBBA). While reasonable people can debate the ‘beauty’ of this bill, at hundreds of pages long, it certainly is big. While most of the Bill is legal jargon and special interest carve outs, there are 12 potential tax savings opportunities that stand out for our clients and/or their families. Please note that each opportunity requires careful planning as the proverbial ‘devil’ is in the details:

  1. “Trump Accounts” for Minors - Yes they are really called ‘Trump Accounts’ (similar to Roth IRA) and will be available to anyone under the age of 18. Children born between Jan 1, 2025 and December 31, 2028 will receive a $1,000 addition from the US Treasury Department. 
  2. 529 College Accounts Expanded - Once limited to college tuition, 529 accounts have again been expanded to include virtually all education expenses.
  3. Standard Deduction Locked In - Set at $15,750 (Single) or $31,500 (Married), there is also a ‘bonus’ deduction of $6,000 per person ages 65+
  4. S.A.L.T. Tax Limit Increased - For at least the next four years, State And Local Taxes can be itemized up to $20,000 (Single) or $40,000 (Married)
  5. Charitable Donations - If you are unable to itemize your deductions (most can’t), you can still deduct $1,000 (Single) or $2,000 (Married) ‘above the line’.
  6. Tax Brackets Locked In - The current tax rates that were set to go up in 2026 have been locked at their current lower levels.
  7. Child Tax Credit Increased to $2,200
  8. Car Loan Interest is now deductible - Subject to several rules, including ‘100% American assembled’, up to $10,000 of interest can be deducted. 
  9. Gambling Losses Limited to 90% - This is less of an opportunity and more of a warning that you can now lose all your money at the casino and still owe taxes.
  10. Estate (and gift) Tax Limited Locked at $15,000,000 each - For 99.9% of people, this simply means you can gift as much as you want to family.
  11. First $25,000 of tips are deductible - Tons of rules on this one, but some tips are now tax deductible.
  12. Some Overtime is deductible - In certain circumstances, $12,500 (Single) or $25,000 (Married) of overtime can be deducted.


**Please Note: Despite what you may have heard, Social Security IS still taxable.**

“It’s a Trap!”

 -ADMIRAL ACKBAR (STAR WARS: RETURN OF THE JEDI, 1983 DOW ~ 1,100)

Hard to believe it’s been more than 40 years since the release of Star Wars. During those decades much has changed, and much is still the same. While things like advances in technology have transformed our lives beyond anyone’s imagination, it has also transformed the ways bad guys can commit crimes.


For example, 40 years ago you may have received a physical letter (or 20-years ago an email) that was poorly written, promising you fame and fortune if you just mailed (or transferred) money to your ‘long lost cousin who is a middle eastern prince willing to send you all his wealth if you just pay the transfer fee…’


With the help of technology (including AI), thieves now know where you live, where you shop, the names of your family members, your last vacation, your date of birth and every other piece of information necessary to convince you to trust them just a little, which is all they need to steal everything.


During our recent client education event, Elliott , Sheridan Culhane from MFS and Ryan Hickel CPA shared how you can protect yourself and F.I.G.H.T. B.A.C.K. against fraud and elder abuse. If you would like the link to the recording of this event, please contact our office and we will email it to you. 


Your best defense, however, is to remember the words of Admiral Ackbar in Star Wars: “IT’S A TRAP!” and whenever you see even a hint of fraud, call our office (847-954-7028) ASAP and our team will always be glad to help determine if it is legitimate

Mark your Calendars!

  1. We'll be having our Q4 Townhall on November 11th, 2025 at 5 PM CT - link is HERE
  2. We'll have our Q1 2026 Townhall on Feb 11th at 5 PM CT
Boy in black Nike sweatsuit leaning on a pipe against a brick wall, pebbles on the ground.

Big milestone for the Vaughn family: Graham, now age two, has officially started preschool. He’s growing fast, singing his ABCs, and showing off his Baby Shark performances at every opportunity — much to Elliott and Ellen’s delight, and to the amusement of their eight-year-old dog Louis.



Ben is loving life in downtown Chicago’s Old Town neighborhood and can often be found cheering on the Blackhawks, Bulls, and Bears.

By Elliott Vaughn July 16, 2025
The Big Beautiful Bill ACT – A Tax Perspective President Trump has signed into law what’s being called the “ Big Beautiful Bill ”—a sweeping piece of tax legislation that touches everything from income brackets and deductions to estate taxes and energy credits. Whenever Washington rewrites the tax code, the media machine kicks into high gear. Cable news fills with shouting heads. The internet lights up. People begin to wonder: Does this change everything for me? The short answer is: probably not. But that doesn’t mean we shouldn’t pay attention. We’re not here to weigh in on whether this is a good bill or a bad one. We’ll leave that to the talking heads. Our job is to help you understand how the key parts of this could affect your personal financial plan—whether you’re still earning, already retired, or planning to leave a legacy. Take a look at our cheat sheet HERE for a breakdown of the key provisions (Big thanks to Toren Tuttle, MBA, CPA, and the team at Retirement Tax Services for their insight as I put this together) But here’s what’s in the bill, in plain English. The Headlines This bill locks in many of the 2017 tax cuts: Income tax brackets remain lower The standard deduction is expanded Business owners retain access to the Qualified Business Income deduction The estate tax exemption rises to $15 million in 2026 The SALT deduction cap temporarily increases, though it’s scheduled to shrink again in 2030 In addition, the bill introduces several new deductions—for seniors, parents, tipped workers, and even car loan interest. Charitable giving rules have also changed: starting in 2026, you can deduct up to $1,000 ($2,000 if married), even if you don’t itemize. Some provisions are going away. Electric vehicle and energy-efficiency tax credits will phase out. The 1099-K reporting threshold for apps like Venmo and PayPal will return to $20,000 and 200 transactions. Gambling loss deductions are being limited. We’ve summarized all of these changes in the cheat sheet. Again, it’s worth keeping handy. The Perspective Here’s what really matters: tax law changes. Planning endures. When tax policy shifts—as it always does—our job is not to react or guess. Our job is to help you make smart, timely decisions within the framework of a long-term plan. We’ve seen this before. In 2001, 2003, 2010, 2017—and now, 2025. The tax code gets rewritten. Markets continue doing what they’ve always done. The political winds change. But your financial plan is built to withstand all of it—if it’s grounded in discipline and purpose. We’ll walk through all of this in more detail at our August Client Townhall. But know this: There is no rush. The ink is barely dry. And as always, we’ll sort through it together. Bottom Line Most of these changes either lock in current tax cuts or introduce new, targeted deductions—especially for seniors and middle-income earners. But many of the new benefits are temporary. So whether you’re still working or already retired, smart tax planning will matter more than ever. What You Should Do Now? Nothing—just yet. But, we’ll help you: Take advantage of temporary deductions before they disappear Maximize charitable giving in tax-smart ways Revisit Roth conversion strategies Coordinate with your CPA to fine-tune your tax plan Update your estate plan while exemptions remain high No panic. No politics. Just planning. We'll be discussing the new Tax Law in our next Townhall on August 5th at 5:30 CT We’ll be ready—and so will you.
The logo for harbor wealth has a lighthouse on it
By Elliott Vaughn April 9, 2025
Every so often, something surfaces that rattles investors’ and our financial news media confidence. A crisis, a conflict, a change in policy. It almost always arrives wrapped in the same seductive phrase: “This time it’s different.” We heard it in 2016 with Brexit. In 2018, it was trade war rhetoric—culminating in a Christmas Eve when the market was down 25%. In early 2020, we endured the swiftest 30% market decline in history—followed almost immediately by the fastest recovery ever recorded. Then came 2022, with the highest inflation in 40 years and the most aggressive interest rate hikes since the 1980s. And now, in 2025, tariffs have once again taken center stage—evoking comparisons to the protectionist policies of the 1930s, and even further back to President McKinley’s platform of the 1890s. So here we are again. Different headlines. Same Reaction Let’s remind ourselves: Wall Street—and the companies it represents—do not care who the president is. Markets have advanced under Democrats and Republicans, through wars, scandals, crises, and recoveries. What matters most is not who sits in the White House, but whether you remain seated in your financial plan. If we’ve learned anything from the past century of market history, it’s this: circumstances change, but average investor behavior stays the same. Panic. Recovery. Growth. Repeat. Now—and this is essential—the enduring 10%+ average annual return of the equity market and its frequent, temporary declines are not two unrelated phenomena. They are part of one indivisible whole. The volatility is not just normal; it is necessary. It is the emotional toll we pay for participating in the long-term wealth-creating miracle of capitalism. Please understand: I do not believe you are the average investor. What I am saying is this: volatility is part of the journey. We planned for it, it's been part of every client review I have conducted. We expect it. A Case in Point: April 7th On April 7th, the market opened down 2%. Then, on the strength of a rumor—a potential 90-day delay in newly announced tariffs—the market surged 8%. Moments later, when the rumor was denied, the gains disappeared just as quickly. Nearly $2.4 trillion in market value evaporated in the space of a few hours, all driven by speculation. I mentioned in our April 3rd email to clients " Market recoveries often happen swiftly, and missing just a handful of the best days can significantly reduce long-term returns " And then, as if to underline the point: on April 9th, the 90 day delay was officially confirmed. The market responded with another sudden move—this time up 9%—even as long-term questions about trade policy remained unresolved. This is not investing. This is emotional voting, fueled by headlines and hearsay. This is what markets do in the short term—they fluctuate, sometimes violently, based on narrative and noise. But over time, markets stop voting and start weighing. They weigh earnings, innovation, productivity, and progress. And those who remain invested in that process—not just through the quiet stretches, but through the storms—are the ones who capture the long-term rewards. The market’s premium return has always been the compensation for enduring this volatility. The declines are not just inevitable—they are indispensable. You cannot have one without the other. (Just look at the S&P 500’s intra-year declines compared to its annual returns graph below.) So no, we will not attempt to time the market. We will not allow momentary fear to dictate lifelong decisions. We will stay the course—because every time we have done so in the past, we’ve been rewarded with what this journey is ultimately about: peace of mind, prosperity, and progress.