Medicare: It’s Not That Complicated

By Boston Hill Advisors on October 6, 2025

Choosing a Medicare Plan that Matches Your Lifestyle and Needs

Understanding Medicare and choosing the right plan can be challenging for many Americans due to its complexities. However, with the right knowledge, first-time Medicare enrollees will be well-equipped to apply during their enrollment period. Plus, if this is not your first time enrolling for Medicare, these insights will also be beneficial if you decide to adjust your Medicare plan.

To help you feel confident during enrollment, we spoke to Ari Parker, Co-Founder and Head of Medicare Advisory at Chapter and author of It’s Not That Complicated: The Three Medicare Decisions to Protect Your Health and Money about the key considerations that 65+-year-olds should make when selecting a Medicare plan.

Understanding Premiums and Fees

High-income earners (single filers who make $103,000 and joint filers who make $206,000) may have to pay a higher premium for Part B (Medical Insurance) and Part D (Medicare drug coverage) called the income-related monthly adjustment amount (IRMAA). The Centers for Medicare & Medicaid Services (CMS) determines this by looking at your tax return from two years prior. However, if you experience a qualifying life change like work stoppage, work reduction, or divorce, you can submit an appeal and have the government look at a more recent year.

Managing Co-insurance Costs

Medicare plans pay 80% of medical costs, leaving you to pay 20% of the rest of the bill. While that may not sound like a lot out-of-pocket, depending on what type of medical procedures you receive, that cost would significantly hurt your finances, especially if you are on a fixed income. To avoid having to pay out-of-pocket, you can opt to purchase Medigap Plans A-N.

Expanding Your Coverage

As stated above, if you already have Original Medicare (Plan A and Plan B), you can select Medigap (Medicare Supplement Plan G) to fill in the co-insurance gaps left by Original Medicare. Medigap is also a great option to expand your coverage geographically. This supplemental insurance is especially beneficial if you travel regularly or have a second home as Medigap can also cover international healthcare. It is important to note that these plans are only offered by private companies.

Find out more about how we, along with Chapter can help you select a Medicare plan that fits your needs by watching the webcast, “Medicare: It’s Not That Complicated!”.

Additionally, please reach out to us if you have any other questions regarding Medicare and enrollment.


Boston Hill Advisors is a group comprised of investment professionals registered with Hightower Advisors, LLC, an SEC registered investment adviser. Some investment professionals may also be registered with Hightower Securities, LLC (member FINRA and SIPC). Advisory services are offered through Hightower Advisors, LLC. Securities are offered through Hightower Securities, LLC.

This is not an offer to buy or sell securities, nor should anything contained herein be construed as a recommendation or advice of any kind. Consult with an appropriately credentialed professional before making any financial, investment, tax or legal decision. No investment process is free of risk, and there is no guarantee that any investment process or investment opportunities will be profitable or suitable for all investors. Past performance is neither indicative nor a guarantee of future results. You cannot invest directly in an index.

These materials were created for informational purposes only; the opinions and positions stated are those of the author(s) and are not necessarily the official opinion or position of Hightower Advisors, LLC or its affiliates (“Hightower”). Any examples used are for illustrative purposes only and based on generic assumptions. All data or other information referenced is from sources believed to be reliable but not independently verified. Information provided is as of the date referenced and is subject to change without notice. Hightower assumes no liability for any action made or taken in reliance on or relating in any way to this information. Hightower makes no representations or warranties, express or implied, as to the accuracy or completeness of the information, for statements or errors or omissions, or results obtained from the use of this information. References to any person, organization, or the inclusion of external hyperlinks does not constitute endorsement (or guarantee of accuracy or safety) by Hightower of any such person, organization or linked website or the information, products or services contained therein.

Click here for definitions of and disclosures specific to commonly used terms.