Medicare at 65: The 6 Mistakes That Cost Oregon Retirees Thousands

By Rodney Cummings, Legacy Wealth Services | June 2026

Turning 65 is a major milestone — and Medicare is one of the most important decisions that comes with it. But the Medicare system is complex, full of deadlines, and easy to get wrong. A single misstep can mean permanent premium penalties, gaps in coverage, or paying thousands more per year than necessary.

Here are the six most common — and costly — Medicare mistakes Oregon residents make, and exactly how to avoid them.

Mistake #1: Missing Your Initial Enrollment Window

Your Initial Enrollment Period (IEP) is a 7-month window: 3 months before your 65th birthday, your birthday month, and 3 months after. Miss this window and you face late enrollment penalties that last for life.

Part B late penalty: 10% added to your premium for every 12-month period you were eligible but didn’t enroll. If you miss by 2 years, your Part B premium increases 20% — permanently.
Part D late penalty: 1% of the national base premium for every month you went without creditable drug coverage. This also lasts for life.

The exception: If you’re still covered by qualifying employer insurance (yours or a spouse’s), you can delay without penalty. But the rules here are precise — retiree coverage, COBRA, and marketplace coverage do NOT count as qualifying coverage.

Mistake #2: Not Understanding the Difference Between Advantage and Supplement Plans

This is the most consequential Medicare choice you’ll make, and it’s poorly understood.

Medicare Advantage (Part C):

Managed care plans (HMO/PPO) offered by private insurers
Often have $0 or low premiums
Typically include drug coverage
Require using network providers
Have copays, coinsurance, and out-of-pocket maximums
Benefits and networks change each year

Medicare Supplement (Medigap):

Covers the “gaps” in Original Medicare (deductibles, coinsurance, etc.)
Higher monthly premiums, but predictable costs
Use any doctor who accepts Medicare — nationwide
No network restrictions
Does NOT include drug coverage (need separate Part D)

The right choice depends on your health, finances, travel habits, and provider preferences. What works for your neighbor may cost you significantly more given your specific situation.

Mistake #3: Choosing a Plan Based Solely on Premium

This one is almost universal. People see a $0-premium Advantage plan and think they’ve found a deal.

What they don’t see: the $6,000–$8,000 annual out-of-pocket maximum. If you have a major health event — a hospitalization, surgery, or serious illness — a Supplement plan with higher premiums can save $4,000–$6,000 that year compared to a $0-premium Advantage plan.

Total cost analysis — not just the monthly premium — is the only way to make an informed choice. This means projecting expected healthcare utilization, comparing out-of-pocket maximums, and accounting for network adequacy for your preferred doctors.

Mistake #4: Forgetting to Review Your Plan Every Year During AEP

Medicare Advantage and Part D plans are not permanent. Every year during the Annual Enrollment Period (AEP) — October 15 through December 7 — your plan can change its premiums, formulary (drug list), network, and benefits.

We regularly see clients whose prescription drugs get removed from their plan’s formulary, meaning they’d pay full price — or whose doctors leave the network. A 30-minute annual review during AEP can save hundreds or thousands of dollars.

Oregon retirees: mark October 15 on your calendar every year. If you have a Medicare advisor (you should), they should be reaching out to you during this window.

Mistake #5: Not Coordinating Medicare with Other Retirement Benefits

Medicare doesn’t exist in isolation. It interacts with:

Social Security timing: When you claim Social Security affects when Medicare Part B premiums are deducted (and IRMAA surcharges if your income is high)
HSA contributions: You cannot contribute to an HSA once you’re enrolled in any part of Medicare. Continuing to contribute after Medicare enrollment creates IRS penalties.
Retiree employer coverage: Understanding how this coordinates with Medicare, which is primary and which is secondary, determines what you actually owe out-of-pocket
Veterans benefits (VA): Having VA coverage doesn’t substitute for Medicare — you generally still want both, and understanding how they work together matters

Mistake #6: Going It Alone

This might be the most expensive mistake of all.

Medicare has dozens of plan options in Oregon. The right answer depends on your zip code, your doctors, your prescriptions, your health history, and your financial situation. A licensed, independent Medicare specialist works with multiple carriers — not just one — and can compare options objectively.

And it doesn’t cost you more. Medicare insurance brokers are compensated by the insurance companies, not by you. You pay the same premium whether you go through a broker or directly to the insurance company.

The difference is that a broker does the comparison work for you, ensures you don’t miss any deadlines, and stays in your corner at renewal time every year.

What to Do If You’re Turning 65 in the Next 12 Months

Start the process 3-4 months before your birthday. This gives time to:

Understand your options without pressure
Compare Supplement vs. Advantage plans for your situation
Evaluate your prescription drug needs
Coordinate with your employer coverage (if applicable)
Enroll during your optimal window

Schedule a no-cost Medicare consultation:

📅 Book a 30-Minute Call with Rodney Cummings

Or explore your Medicare options at legacywealthservices.com/medicare

Rodney Cummings is a licensed Medicare insurance professional serving Oregon residents turning 65 and navigating Medicare for the first time. Legacy Wealth Services is independent, working with multiple carriers to find the right fit — not just the plan that pays us more.