
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:
- “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.
- 529 College Accounts Expanded - Once limited to college tuition, 529 accounts have again been expanded to include virtually all education expenses.
- 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+
- 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)
- 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’.
- Tax Brackets Locked In - The current tax rates that were set to go up in 2026 have been locked at their current lower levels.
- Child Tax Credit Increased to $2,200
- Car Loan Interest is now deductible - Subject to several rules, including ‘100% American assembled’, up to $10,000 of interest can be deducted.
- 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.
- 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.
- First $25,000 of tips are deductible - Tons of rules on this one, but some tips are now tax deductible.
- 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!
- We'll be having our Q4 Townhall on November 11th, 2025 at 5 PM CT - link is HERE
- We'll have our Q1 2026 Townhall on Feb 11th at 5 PM CT
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.


