The Medicare Enrollment Kit

Medicare enrollment is unforgiving. Miss your Initial Enrollment Period and you could pay a 10% penalty on Part B premiums for the rest of your life — for each year you delayed. Pick the wrong plan type (Advantage vs Medigap) and switching later may be medically underwritten, expensive, or impossible.

Get it right the first time. That is what this kit is for.

WHAT'S INSIDE — 29 PAGES:

- All four parts (A, B, C, D) explained in plain English

- All five enrollment windows — IEP, GEP, SEP, OEP, AEP

- The Medigap vs Medicare Advantage decision chapter with full tradeoff analysis

- The switch-back warning (why choosing at 65 matters so much)

- Working past 65 and the 20-employee rule

- COBRA coverage gap mechanics (where many people get trapped)

- HSA contribution rules with the 6-month lookback

- Part D plan selection strategy and the annual Plan Finder habit

- AEP review checklist — what to review each October

- Full enrollment checklist broken by months-before-birthday

- Plan comparison worksheet

- Four phone scripts (SSA, Medigap insurer, 1-800-MEDICARE, HR creditable coverage)

- Top 10 enrollment mistakes

SIX REAL CASE STUDIES:

- Linda's clean IEP enrollment (the right way)

- Robert's $20,500 late-enrollment penalty horror from COBRA confusion

- Maria's Medicare Advantage cancer diagnosis disaster

- David & Susan's coordinated enrollment across different ages

- James's Special Enrollment Period from COBRA done correctly

- Patricia's $6,220 IRMAA surprise from a rental sale

WHO IT'S FOR:

- Anyone approaching their 65th birthday (start reading 9 months before)

- Anyone already on Medicare wondering if they picked the right plan

- Retirees still working past 65 who need to navigate the employer-coverage overlap

- Couples coordinating Medicare across different ages

- Anyone who has ever been confused about Medigap vs Advantage

FORMAT: PDF, 29 pages, instant download. Readable on any device.

All content is educational reference material and is explicitly not personalized financial advice.

Written by Rabbi Mizrahi.