
Key takeaway: Helping a loved one with Medicare takes more than good intentions — this checklist shows you exactly what's in place and what still needs attention before you make any coverage decisions together.
Example 1: Daughter helping her 68-year-old mother move from employer coverage to Medicare. After running through the checklist, the readiness score comes back 4 out of 10. The daughter has a general sense of her mother's health situation, but several critical pieces are missing. There's no copy of the Medicare card on file, no written medication list with dosages, no documented list of preferred doctors, and no conversation yet about how much her mother can comfortably spend on premiums each month. Most importantly, there's no healthcare power of attorney in place — meaning if her mother became incapacitated before enrollment was complete, the daughter would have no legal standing to make decisions. The checklist flags these five gaps and suggests addressing the legal document first, since it takes time to execute and nothing else can move forward without it.
Example 2: Son helping his 72-year-old father switch Medicare Advantage plans during AEP. This family is in much better shape — readiness score of 7 out of 10. The son has a copy of his father's Medicare card, knows his income, and has the current MA plan card. The gaps are more subtle but still matter a lot: he hasn't checked whether his father's three specialists are in-network under the new plan, and he hasn't pulled up the formulary to confirm his father's two brand-name medications are covered at a reasonable tier. These omissions could mean surprise bills after January 1. The checklist flags both as high-priority before the December 7 deadline.
Example 3: Caregiver for an 80-year-old parent with dementia. Readiness score: 3 out of 10. This situation requires the most attention. The parent can no longer participate in coverage decisions, but no legal documents exist to authorize the caregiver to act on their behalf. There's no durable power of attorney, no healthcare proxy or healthcare proxy declaration, and no advance directive on file. On top of that, the medication list is incomplete — the parent sees a neurologist, a cardiologist, and a primary care physician, and the medications from each haven't been reconciled into one master list. The checklist recommends starting with an elder law attorney to establish legal authority, then scheduling a care coordination meeting with the primary care doctor to create a full medication and diagnosis record before any coverage decisions are made.
| Scenario | Input | Result |
|---|---|---|
| New to caregiving, loved one turning 65 | No legal docs, no medication list, no Medicare card yet | Readiness score: 2–4/10. Priority: POA, medication list, Medicare card copy |
| AEP plan switch, most documents in hand | Has Medicare card, income info, current plan card; missing formulary check | Readiness score: 6–7/10. Priority: verify doctors and drugs in new plan before Dec 7 |
| Loved one with cognitive decline | No POA, incomplete medication list, multiple specialists | Readiness score: 2–3/10. Priority: legal authority first, then care coordination |
| Experienced caregiver, annual review | All docs current, POA in place, medications verified | Readiness score: 9–10/10. Ready to compare plans confidently |
| Decision area | Tool | What it answers |
|---|---|---|
| Enrollment | Initial Enrollment Period Calculator | When your 7-month Medicare eligibility window begins and ends based on your 65th birthday |
| Enrollment | When Should I Sign Up for Medicare? | The best time to enroll based on your work status, other coverage, and age |
| Enrollment | Special Enrollment Period Checker | Whether a life event qualifies you for enrollment outside the standard windows |
| Enrollment | Late Enrollment Penalty Checker | How much extra you'll pay monthly if you missed your enrollment window |
| Enrollment | Part B Penalty Calculator | The exact 10%-per-year premium increase for delayed Part B enrollment |
| Enrollment | Part D Penalty Calculator | The 1%-per-month premium increase for gaps in creditable drug coverage |
| Costs | Cost Scenario Planner | Estimated annual spending across plan types at different health utilization levels |
| Costs | Advantage vs. Medigap Cost Comparison | True cost difference between Medicare Advantage and Original Medicare with Medigap |
| Costs | IRMAA Calculator | Whether your income triggers higher Part B and Part D premiums |
| Costs | Part A Premium Estimator | Your monthly Part A premium based on work history and quarters of coverage |
| Costs | M3P Calculator | How the Medicare Prescription Payment Plan smooths your drug costs into monthly payments |
| Coverage | Doctor & Drug Assessment | Whether your providers and prescriptions are covered by a specific plan |
| Coverage | Part D Shopping Tool | Which Part D plan has the lowest total annual cost for your specific medications |
| Coverage | Travel & Network Risk Assessment | How your coverage works outside your home area and which plan types travel best |
| Employer/COBRA | COBRA vs. Medicare | Why COBRA can trigger permanent Medicare penalties and how costs compare |
| Employer/COBRA | Employer Coverage vs. Medicare | Whether your employer plan or Medicare is primary and when to transition |
| Employer/COBRA | HSA & Medicare Compatibility | How Medicare enrollment affects HSA eligibility and what to do before enrolling |
| Planning | Caregiver Readiness Checklist | Whether you have everything in place to help a loved one with Medicare decisions |
| Planning | Document Gatherer | Which documents you need to have ready before enrolling or changing plans |
| Planning | Medigap Fit Assessment | Whether Medigap or Medicare Advantage is the better fit for how you use healthcare |
| Planning | Medigap Open Enrollment Window | Whether you're inside your one-time guaranteed issue window for Medigap |
| Planning | Medicare Savings Program Eligibility | Whether your income qualifies you for help paying Medicare premiums and cost-sharing |

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