Medicare Made Simple: Key Decisions You Should Understand

At WiseOak, our work has always gone beyond investment management. 

We want you to understand the why behind your financial decisions because real confidence doesn’t come from reacting under pressure but from being prepared long before the moment of choice.

Most of that clarity is built through our ongoing conversations. But some topics require deeper, specialized guidance. Rather than wait until you’re already facing a complex decision, we started bringing trusted experts directly to you.

That’s how our WiseOak Expert Series began.

For our first session on November 20th, we focused on Medicare, which is one of the most important decisions in retirement, and one of the easiest to misunderstand. Juliana Souza, a licensed Medicare agent, walked us through the key pieces, the real costs, and the choices that tend to surprise people.

Below is a streamlined, easy-to-follow guide to what matters most.

How Medicare Is Structured and What You’re Really Paying For

Medicare has four main pieces. Most people know the letters, but not what they actually cover:

·       Part A: hospital coverage; usually free if you’ve worked 40 quarters.

·       Part B: outpatient care; starts around $185 annually. Delaying it without credible coverage triggers a 10% penalty per year.

·       Part D: prescription drug coverage; typically $0–$100/month, with a 1% monthly penalty for late enrollment.

·       Part C (Medicare Advantage): private plans that bundle A, B, and usually D.

For higher-income households, IRMAA adds extra monthly premiums. For 2025, that begins at $106,000 (single) or $212,000 (joint) and can push Part B premiums into the $600+ range.

Even with Medicare, you’re still responsible for 20% of costs and there’s no cap. With deductibles of $1,700 for Part A and $288 for Part B (2026), hospital stays can become expensive quickly.

Medicare Supplement Plans: What Fills the Gaps

Supplement plans (also called Medigap) are designed to cover the 20% that Original Medicare leaves behind.

Two plans tend to rise to the top:

·       Plan G: the most comprehensive option for new enrollees; covers everything except the Part B deductible.

·       Plan N: lower premiums but includes small copays and doesn’t cover Part B excess charges.

Coverage is standardized by law, no matter the company. The real difference is price stability. Some carriers increase premiums 15–30% a year. Others hold increases closer to 0–3% for years. The latter often saves clients far more over time.

Premiums also vary by zip code, age, and gender.

Medicare Advantage (Part C): Attractive on Paper, But Know the Trade-offs

Advantage plans are marketed heavily because many offer $0 premiums, include dental and vision, and package drug coverage. But the limitations matter:

• Coverage is tied to your county, not the nationwide Medicare network.
• Referrals and prior authorizations are common.
• Networks and copays reset each year.
• Some plans are being eliminated entirely.

Out-of-pocket maximums typically land between $10,000 and $14,000.

Juliana also noted a growing concern: major providers like Mayo Clinic and Moffitt no longer accept Advantage plans, and PPO options are shrinking so quickly that some counties now have none.

Advantage can be a helpful option if supplement premiums aren’t affordable. But if you hope to switch back to Original Medicare with a supplement later, it’s usually easier to do so before your mid-70s, when underwriting is more forgiving.

How Drug Coverage Works Under Medicare

Regardless of whether you stay with Original Medicare or choose an Advantage plan, the drug benefit works the same:

• Tier 1 (preferred generics): usually $0
• Tier 2: generally $5–$10
• Tiers 3–5: subject to a $615 deductible, then 25% coinsurance

Once you reach $2,000 out of pocket, your medications are fully covered for the rest of the year.

There’s also a Prescription Payment Plan that spreads the $2,000 maximum over 12 months.

Underwriting Rules That Catch People Off Guard

This is one of the most misunderstood parts of Medicare.

At 65, you get a six-month window where you can buy any supplement plan with no health questions, no underwriting.

After that:

• Medicare Advantage never asks health questions.
• Supplement plans almost always do.

Underwriting has tightened significantly. Common conditions and even certain medications can lead to denials. That’s why the timing of your decisions matters.

Enrollment Timing — Especially if You Work Past 65

If you’re already collecting Social Security, Medicare enrollment is automatic.

Otherwise, you have a seven-month window around your 65th birthday. Miss it, and you’ll wait until the next January–March enrollment period and may face penalties.

If you’re still working:

·       20+ employees: you can delay Part B without penalty.

·       Fewer than 20: Medicare becomes primary, and delaying Part B can get expensive.

COBRA, VA benefits, retiree health plans, and private insurance do not count as credible coverage for delaying Medicare.

When you eventually enroll, you’ll need forms CMS 40B and CMS L564 and processing can take 4–8 weeks.

Doctor Access and the Risk of Going Without a Supplement

About 98% of doctors nationwide accept Original Medicare. Certain areas like California, New York, a few large cities have exceptions, but they’re rare.

Going without a supplement leaves you exposed to unlimited 20% coinsurance. We’ve seen single hospital visits resulting in $6,000+ out-of-pocket, with more bills to follow.

Advantage plans cap costs, but the caps are still high.

Coverage When Traveling

A quick overview:

• Original Medicare + Supplement: nationwide
• Advantage HMO: emergencies only
• Advantage PPO: some flexibility, but still limited

One real-life example: a client of Juliana’s needed retinal surgery out of state. Because he left the ER and returned the next morning, the procedure wasn’t covered under his Advantage plan. The nuance matters.

What We Hope You Take Away

Medicare is one of those areas where informed choices truly matter. 

Knowledge is power, and bringing experts into these conversations is one way we help you stay ahead of decisions that can shape both your health and your long-term financial wellbeing. 

If you’re looking for a deeper understanding or want to share this resource with someone who might benefit, we’re always glad to be a source of guidance and support.

Juliana Souza is an independent licensed Medicare agent and is not affiliated with WiseOak Wealth Management, Mutual Advisors, LLC, or any of their subsidiaries or affiliates. Her participation in the WiseOak Expert Series is solely for educational purposes and should not be interpreted as an endorsement of any specific products or services.

Investment advisory services offered through Mutual Advisors, LLC DBA Wise Oak Wealth, a SEC registered investment adviser.