Income Strategy, Medicare, and the Florida Advantage Q&A
By Todd Stankiewicz | CIO, SYKON Capital | Portfolio Manager, Free Markets ETF (FMKT)
There is a lot of noise out there about whether retiring in Westchester County is actually realistic, and we hear the question constantly. SYKON Capital is a national firm with offices in both Westchester County, NY and Jupiter, Florida, and we work with pre-retirees and retirees navigating this exact question every day. Below are 3 of the questions we field most often, with the kind of straight, experience-based answers we share with our clients.
Q4: What is IRMAA, and why does it matter so much for Westchester County retirees?
IRMAA, the Income-Related Monthly Adjustment Amount, is an additional surcharge layered on top of your standard Medicare Part B and Part D premiums that kicks in once your income crosses certain thresholds. In 2026, the standard Medicare Part B premium is $202.90 per month. When your income crosses the first IRMAA bracket, that number jumps, and it scales up from there in tiers. For a married couple facing multiple IRMAA brackets, the cumulative annual premium impact can be substantial.
Here is what catches most people off guard: the Social Security Administration uses your tax return from two years prior to determine your IRMAA. So in 2026, your Medicare costs are calculated based on your 2024 income. That means if your last full year of work produced high income, you could be paying elevated Medicare premiums in the very first years of retirement, even though your income has already dropped significantly.
The good news is there is a formal appeal process. Retirement itself qualifies as a life-changing event, and you can file Form SSA-44 directly with the Social Security Administration to have them use your more current, lower retirement income instead. We walk clients through this process regularly, and while many clients have experienced meaningful savings, individual results vary based on specific circumstances and planning.
The longer strategy is managing your income thoughtfully throughout retirement to stay below key IRMAA thresholds. That means being intentional about the size and timing of IRA withdrawals, considering Roth conversions (generally recommended before age 63 given the 2-year lookback), and treating every income decision as interconnected, because in retirement, they are.
Q5: When is the right time for a Westchester retiree to collect Social Security?
I have a strong view on this: in our experience, most people claim Social Security too early, and in many cases it can cost them significantly more over their lifetime than they ever anticipated. Every year you delay claiming past your full retirement age, your benefit grows by approximately 8% per year, all the way up to age 70. That is a federally backed, inflation-adjusted benefit that cannot be outlived. In our view, very few income sources in a retirement portfolio offer a comparable combination of inflation protection, longevity coverage, and predictability.
In a high-cost environment like Westchester County, Social Security functions as a financial floor. The higher that floor is, the less pressure there is on your investment portfolio to generate income, which matters enormously during down markets and over a multi-decade retirement. Delaying is, in our view, one of the most powerful tools available for protecting against outliving your money.
Not everyone can afford to wait, and we understand that. That is where the bridge strategy becomes essential: drawing down other assets (taxable accounts, managed IRA distributions, or Roth accounts) to cover expenses while you delay Social Security. This requires a real plan, but when executed well, the long-term impact on total retirement income can be significant.
There is also a direct intersection with IRMAA and STAR planning here. The income you take during those bridge years affects your Medicare costs and your property tax exemption eligibility. These decisions are not made in a vacuum: they need to be coordinated across your entire financial picture, and that is exactly the kind of multi-variable planning where having a dedicated advisory team makes a measurable difference.
Q6: Is Westchester County a smart base for snowbirds who want to split time between New York and Florida?
In my view, this is one of Westchester's most underappreciated retirement advantages, and I can speak to it directly, because we have offices in both Westchester County, New York and Jupiter, Florida. We see this lifestyle work extremely well for clients on both ends of the equation.
Westchester County Airport in White Plains (HPN) offers nonstop flights directly to Palm Beach International Airport. The flight time is roughly under 3 hours. If you live in Harrison, Rye, Rye Brook, or the surrounding areas, you can be at that airport in 15 to 20 minutes. No JFK crawl. No LGA parking nightmare. No sitting in traffic on the Van Wyck hoping you make your flight. You park at a manageable, stress-free airport and you are in Palm Beach the same day, relaxed.
There is also a genuinely meaningful financial dimension to the snowbird strategy. If you spend more than 183 days per year in Florida, you may qualify to establish Florida as your primary state of residence. Florida has no state income tax. For a retiree with significant income, that can represent real savings over time. While Florida offers no state income tax, retirees should also consider other factors such as healthcare costs, insurance costs and climate differences when evaluating this option. Establishing Florida domicile does require proper documentation (driver's license, voter registration, updated estate planning), but for the right client, the financial benefit over a long retirement can be substantial.
We believe the Westchester-to-Florida lifestyle is not just a comfort strategy: it can be a financially strategic one for the right retirees. And having advisors who understand both markets, maintain relationships in both communities, and have seen these transitions play out for real clients is an advantage that is genuinely hard to replicate.
If you are thinking through retirement in Westchester County and want to understand how these strategies apply to your specific situation, we invite you to reach out to the team at SYKON Capital. Clarity first. Confidence follows.
About Author
Todd Stankiewicz | Chief Investment Officer, SYKON Capital
Todd Stankiewicz is the Chief Investment Officer of SYKON Capital, a fee-based registered investment advisor with offices in Westchester County, NY and Jupiter, FL. He is a recurring guest on Fox Business and the Schwab Network, where he discusses markets, portfolio strategy, and investor behavior. Todd is also the portfolio manager of the Free Markets ETF (FMKT).
Learn more at www.sykoncapital.com
Investment advisory services offered through SYKON Capital, LLC, a Registered Investment Advisor with the U.S. Securities and Exchange Commission.
This material is intended for informational purposes only. It should not be construed as legal or tax advice and is not intended to replace the advice of a qualified attorney or tax advisor. This information is not an offer or a solicitation to buy or sell securities. The information contained may have been compiled from third party sources and is believed to be reliable. Please note that contacting us does not establish a client-advisor relationship, and we may receive compensation for advisory services. Personalized advice should be obtained before making financial decisions. Our advice is based on our experience and relationships in both markets. Investment advisory services are offered through SYKON Capital, LLC, a Registered Investment Advisor. Contact us for personalized advice.'
