Medicare doesn't have to be confusing. Let's make it clear.
Winegar Insurance helps people approaching 65 — and those already on Medicare — understand their options, compare plans from most major carriers, and choose coverage that fits their health, their doctors, and their budget. Education first. No pressure, ever.
Advice that connects Medicare to the rest of your retirement
Most Medicare agents look at plans. Clark Winegar looks at the whole picture — how your Medicare choices interact with Social Security timing, retirement income, and IRMAA surcharges.
Independent & broad
We represent most major Medicare Advantage and Medicare Supplement carriers in your area, so the comparison starts from your needs — not one company's product shelf.
Credentialed guidance
Clark is a CFP® professional and a Registered Social Security Analyst (RSSA®), which means Medicare advice grounded in real retirement planning — not just plan brochures.
Help at no cost to you
Our services are free to you. Brokers are paid by insurance carriers at standardized rates, so your premium is the same whether you use us or go direct.
Find your situation
01 Turning 65 soon
You have a 7-month window to enroll, and the choices you make now can follow you for life. Learn what to do, and when.
02 Working past 65
Employer coverage changes the rules. We'll help you avoid late penalties and decide whether to delay Part B.
03 Already on Medicare
Plans change every year. An annual review during open enrollment can lower costs or improve coverage.
The Winegar Medicare Library
Medicare Basics
Parts A, B, C, and D in plain English — what each covers and what it costs.
Advantage vs. Supplement
The single biggest decision on Medicare. Understand the trade-offs before you choose a path.
Prescription drug coverage
How Part D works in 2026, including the $2,100 out-of-pocket cap on covered drugs.
Medicare & Social Security
How the two programs connect — premiums, timing, and the IRMAA income surcharge.
Have a Medicare question?
Get a straight answer in a free, no-obligation conversation with Clark.
Medicare Basics: Parts A, B, C & D Explained
Medicare is the federal health insurance program for people 65 and older, and for some younger people with disabilities. It's built from four parts — and understanding what each one does is the foundation for every decision that follows.
Part A Hospital Insurance
Covers inpatient hospital stays, skilled nursing facility care, hospice, and some home health care.
- Premium-free for most people who worked and paid Medicare taxes for 10+ years
- Has a deductible per benefit period, plus coinsurance for long stays
Part B Medical Insurance
Covers doctor visits, outpatient care, preventive services, lab work, and durable medical equipment.
- Monthly premium set each year by Medicare (higher earners pay more via IRMAA)
- After the annual deductible, Medicare generally pays 80% — you pay 20% with no cap, unless you add coverage
Part C Medicare Advantage
Private plans that bundle Parts A and B — and usually D — into one plan, often with extras like dental, vision, and hearing.
- Many plans have low or $0 additional premium
- You use the plan's provider network and its cost-sharing rules
Part D Prescription Drugs
Private plans that cover prescription medications — either standalone (with Original Medicare) or built into an Advantage plan.
- Late enrollment penalty applies if you go without creditable drug coverage
- Annual out-of-pocket spending on covered drugs is now capped
Two paths to complete coverage
| Path | What it looks like | Best suited for |
|---|---|---|
| Original Medicare + Medigap + Part D | Predictable costs, see any doctor nationwide who accepts Medicare, higher monthly premium | People who value flexibility, travel, or want maximum provider choice |
| Medicare Advantage (Part C) | Lower monthly premium, network-based care, extra benefits, pay-as-you-go costs up to an annual max | People comfortable with a network who want lower fixed monthly costs |
Neither path is "right" for everyone — the fit depends on your doctors, prescriptions, health, budget, and travel plans. That's exactly what a consultation walks through.
Turning 65: Your Medicare Checklist
Your Initial Enrollment Period (IEP) is a 7-month window: the 3 months before your birthday month, your birthday month, and the 3 months after. Here's how to use it well.
1 6+ months out
- Confirm your Part A/B eligibility at ssa.gov
- Decide whether you'll keep working and keep employer coverage
- List your doctors and prescriptions
2 3 months out
- Enroll in Parts A and B (if not automatic)
- Compare the two coverage paths: Advantage vs. Supplement
- Check drug plans against your medication list
3 Birthday month
- Confirm coverage start dates and cards arrived
- Set up premium payments
- Schedule your "Welcome to Medicare" preventive visit
Three mistakes we help people avoid
Missing the window
Enrolling late in Part B or Part D can trigger lifetime premium penalties. If you're not taking Social Security yet, enrollment is not automatic.
Guessing on drug coverage
Even if you take no medications today, skipping creditable drug coverage starts a penalty clock that follows you for life.
Ignoring the Medigap guarantee
When you first join Part B, you can buy any Medicare Supplement with no health questions. That door can close later.
Medicare Advantage (Part C), Explained
Medicare Advantage plans are offered by private insurance companies approved by Medicare. When you join one, the plan delivers your Part A and Part B benefits — and usually your drug coverage — through its own network and cost structure.
How Advantage plans work
What you typically get
- All Part A and Part B covered services
- Usually built-in Part D drug coverage
- An annual out-of-pocket maximum (a cap Original Medicare alone doesn't have)
- Often extras: dental, vision, hearing, fitness benefits, OTC allowances
What to weigh carefully
- Provider networks (HMO/PPO) — are your doctors in-network?
- Prior authorization requirements for some services
- Copays and coinsurance as you use care
- Plans and networks can change every calendar year
HMO vs. PPO at a glance
| HMO | PPO | |
|---|---|---|
| Network | In-network care only (except emergencies) | Out-of-network allowed at higher cost |
| Referrals | Often required for specialists | Usually not required |
| Premium/costs | Typically lowest | Typically somewhat higher |
Medicare Supplement (Medigap) Plans
Medigap plans work alongside Original Medicare, paying some or all of the costs Medicare leaves behind — deductibles, coinsurance, and that uncapped 20%. Plans are standardized by letter (Plan G, Plan N, and so on), so a Plan G's benefits are identical across companies; only price and service differ.
Why people choose Medigap
Freedom of choice
See any doctor or hospital in the U.S. that accepts Medicare. No networks, no referrals — valuable for travelers and snowbirds.
Predictable costs
Higher fixed monthly premium, but very little out-of-pocket exposure when you actually need care.
Stable benefits
Standardized benefits don't change year to year the way Advantage plan designs can.
The two most popular plans
| Plan | How it works | Good to know |
|---|---|---|
| Plan G | Covers essentially everything after you pay the annual Part B deductible | The most comprehensive plan available to those new to Medicare |
| Plan N | Lower premium; you pay small copays for some office and ER visits, plus possible Part B excess charges | A strong value for people comfortable with modest copays |
Because benefits are standardized, shopping Medigap is largely about premium, rate-increase history, and company stability. As an independent agency representing most major supplement carriers, that comparison is exactly what we do.
Part D: Prescription Drug Coverage
Part D plans are offered by private companies and cover prescription medications. You can get drug coverage as a standalone plan alongside Original Medicare, or built into most Medicare Advantage plans.
What changed — and why it matters
An annual cap on drug costs
Out-of-pocket spending on covered Part D drugs is now capped each year ($2,100 in 2026). Once you reach the cap, you pay nothing more for covered drugs that year — a major protection that didn't exist a few years ago.
Spread your costs monthly
The Medicare Prescription Payment Plan lets you spread out-of-pocket drug costs across the calendar year in monthly amounts instead of paying large sums at the pharmacy counter.
How to pick the right drug plan
- Formulary first: confirm every medication you take is covered, and at what tier
- Pharmacy network: "preferred" pharmacies can mean dramatically lower copays
- Total annual cost: premium + deductible + copays — never judge a plan on premium alone
- Re-shop every year: formularies and pricing change annually; last year's best plan may not be this year's
Medicare Enrollment Periods & Deadlines
Medicare runs on windows. Know which one applies to you, and the whole process gets simpler — and cheaper.
| Enrollment period | When | What you can do |
|---|---|---|
| Initial Enrollment (IEP) | 7 months around your 65th birthday | Enroll in Parts A, B, D, an Advantage plan, or Medigap (guaranteed issue) |
| Annual Enrollment (AEP) | October 15 – December 7 | Join, switch, or drop Advantage and Part D plans for January 1 |
| MA Open Enrollment (OEP) | January 1 – March 31 | One switch between Advantage plans, or back to Original Medicare + Part D |
| Special Enrollment (SEP) | Triggered by life events | Losing employer coverage, moving, plan changes, and more |
| General Enrollment (GEP) | January 1 – March 31 | Enroll in Part B if you missed your IEP (penalties may apply) |
Working past 65: the special enrollment path
If you delayed Part B because of active employer coverage (yours or your spouse's, employer with 20+ employees), you get an 8-month Special Enrollment Period when that employment or coverage ends — whichever comes first. Enroll during it and you avoid the late penalty entirely. COBRA and retiree coverage do not count as active employer coverage for this purpose, a detail that catches many people off guard.
Why an annual review matters
- Advantage and Part D plans revise premiums, networks, formularies, and benefits every January
- Your health and prescriptions change too — last year's fit may quietly become this year's overspend
- A 20-minute review each fall confirms you're still in the right plan, or finds a better one
Medicare & Social Security: Two Decisions, One Plan
Medicare and Social Security are separate programs — but they're deeply connected, and coordinating them well can be worth tens of thousands of dollars over a retirement. As a Registered Social Security Analyst (RSSA®) and CFP® professional, Clark looks at both decisions together.
Where the two programs intersect
Premiums come out of your check
If you receive Social Security, your Part B (and often Part D) premiums are deducted automatically. If you delay Social Security, you'll pay Medicare directly — and enrolling in Medicare at 65 is on you, not automatic.
Claiming age ≠ Medicare age
You can claim Social Security anywhere from 62 to 70, but Medicare eligibility starts at 65 for most people. Delaying Social Security to grow your benefit does not mean you should delay Medicare.
IRMAA: the income surcharge
Higher-income households pay more for Parts B and D through IRMAA, based on your tax return from two years prior. Retirement income moves — Roth conversions, large withdrawals, a home sale — can trigger it. Planning ahead (and appealing after life changes) can reduce or avoid it.
The hold-harmless connection
For most beneficiaries, Part B premium increases can't reduce your Social Security check from one year to the next — one more reason the timing of both decisions is worth mapping together.
What an RSSA® roadmap covers
- Optimal claiming age analysis for you (and spousal/survivor coordination)
- How earnings, pensions, and taxes affect your benefit
- Medicare enrollment timing layered onto your claiming strategy
- IRMAA exposure and ways to manage it
For Financial Advisors: Medicare Planning for Your Clients
Healthcare is one of the largest and least-planned expenses in retirement — and Medicare mistakes (late penalties, IRMAA surprises, missed Medigap windows) land squarely in the middle of the financial plans you build. Winegar Insurance partners with advisors to integrate Medicare planning into your process, so your clients get expert guidance and you stay focused on the plan.
How the partnership works
1 You refer
Introduce clients approaching 65, retiring, or facing a coverage change. We handle scheduling and preparation.
2 We advise
Plan comparison across most major carriers, enrollment execution, IRMAA review, and annual re-shopping — documented so you stay informed.
3 Your plan stays whole
Your client's healthcare costs get real numbers, your projections improve, and the relationship stays yours.
Why advisors work with Clark
- Speaks your language: CFP® professional who understands how Medicare decisions ripple through income plans, Roth strategies, and tax brackets
- Social Security depth: RSSA® analysis that complements — not competes with — your planning work
- Independent: broad carrier representation means recommendations driven by client fit
- No cost to you or your client: compensation comes from carriers at standardized rates
Meet Clark Winegar
Clark Winegar founded Winegar Insurance with a simple belief: people deserve to understand Medicare before they choose it.
Clark helps simplify Medicare for seniors and works with financial advisors to integrate Medicare planning into their clients' retirement processes. He is a CFP® professional and a Registered Social Security Analyst (RSSA®), bringing a planning-first perspective to decisions most agencies treat as a sales transaction.
As an independent broker, Clark represents most major Medicare Advantage and Medicare Supplement insurance carriers, which means recommendations start from your doctors, your prescriptions, and your budget — not a single company's products.
- CFP® — Certified Financial Planner™ professional
- RSSA® — Registered Social Security Analyst
- Independent: most major Advantage & Supplement carriers represented
- Education-first, no-pressure approach — always free to you
Contact Winegar Insurance
Phone: (555) 555-5555
Email: [email protected]
Hours: Monday–Friday, 9am–5pm
Free consultation. Bring your questions, your doctor list, and your prescriptions — leave with clarity.
Call NowFrequently asked questions
How much does it cost to work with Winegar Insurance?
Nothing. Brokers are compensated by insurance carriers at rates standardized by Medicare rules, so your premium is identical whether you enroll through us or directly with a carrier. The difference is that with us, you get comparison, guidance, and a person to call.
Are you tied to one insurance company?
No. We're independent and represent most major Medicare Advantage and Medicare Supplement carriers in the areas we serve, so we can compare broadly and recommend what fits you.
I'm already on a plan. Can you still help?
Yes. We review existing coverage every year during the Annual Enrollment Period (Oct 15 – Dec 7) and whenever a life change opens a Special Enrollment Period. Many clients come to us after choosing a plan on their own.
Do I have to change plans if we talk?
Never. Many reviews end with "you're in the right plan — stay put." Education is the product; enrollment only happens if a change genuinely helps you.
What should I bring to a consultation?
Your Medicare card (if you have one), a list of your doctors, your prescriptions with dosages, and any current insurance cards. That's enough for a complete comparison.
Ready when you are
One conversation is usually all it takes to know where you stand.