+1 Thinking Trick · Issue #1 · a little more advanced

Have AI Research Medicare Advantage vs. Medigap, With Sources

Medicare Open Enrollment runs October 15 to December 7. Instead of wading through mailers, have an AI “deep research” tool spend 10 to 30 minutes reading official sources and write you a plain-English report comparing Medicare Advantage and Medigap for your situation, with links you can check. Then take it to a free Medicare counselor.

Why it's useful

Choosing between Medicare Advantage and Original Medicare with a Medigap plan is one of the biggest money-and-health decisions of retirement, and the mailbox fills up with ads every fall. A deep research tool works differently from regular chat: it reads dozens of web pages, then writes an organized report with the sources listed, so you can see where each claim came from. Used well, it turns a confusing pile of information into a short list of smart questions for a real, unbiased counselor.

What you'll need

How to open deep research

Deep research is a special mode, not the regular chat box. In ChatGPT, sign in, then look in the + menu (or Tools) next to the message box for Deep research. In Gemini, sign in and look under Tools (or Upload & tools) for Deep Research. Menus move around, so if you don't see it, type “How do I start deep research?” into the chat.

Also works in: Gemini Deep Research (free, limited) or Claude Research (Claude Pro).

Step by step

1. Jot down your situation, not your identity: your ZIP code (not your street address), your current coverage, the medicines you take, the doctors and hospitals you want to keep, whether you travel or spend winters elsewhere, and a rough monthly budget.
2. Open ChatGPT and sign in. (Trying it free? Use Gemini at gemini.google.com and sign in with your Google account.)
3. Turn on deep research: click the + or Tools button next to the message box and choose Deep research (Gemini: Deep Research).
4. Copy the prompt below with the blue button, paste it in, and fill in the [square brackets].
5. Answer its questions. Deep research often asks a few clarifying questions before it starts. Answer them the same way: situation, not identity.
6. Go get a cup of coffee. The report usually takes 10 to 30 minutes. You can close the window and come back; it keeps working.
7. Read the report and click a few sources. Make sure the important claims point to Medicare.gov, your state's insurance department, or another trustworthy source, and not to a company trying to sell you a plan.
8. Take it to a pro before you decide. Bring the report and its questions to your free State Health Insurance Assistance Program (SHIP) counselor (find yours at shiphelp.org) or call 1-800-MEDICARE. Check actual plan prices at Medicare.gov/plan-compare. Changes must be made by December 7.

The prompt to copy and paste

Press the button to copy it. Then paste it into the deep research box. Replace anything in [square brackets] with your own details.

Please research and write a plain-English report comparing Medicare Advantage with Original Medicare plus a Medigap (Medicare Supplement) plan, for my situation. I am not asking you to choose a specific plan for me. I want to understand the trade-offs so I can talk to a counselor.

My situation:
- ZIP code / county and state: [e.g., 49506, Kent County, Michigan]
- Current coverage: [e.g., Original Medicare + Medigap Plan G + Part D / a Medicare Advantage HMO / new to Medicare]
- Medicines I take: [list names, or say "a few common generics"]
- Doctors and hospitals I want to keep: [names, or "flexible"]
- Health in general terms: [e.g., generally healthy / one chronic condition / frequent specialist visits]
- Travel: [e.g., I spend winters in Florida / rarely travel]
- Rough budget for premiums and out-of-pocket costs: [e.g., about $250/month]

Please include:
1. A one-paragraph bottom line in plain English.
2. A side-by-side table: monthly premiums, out-of-pocket maximums, doctor networks, prior authorization, drug coverage, extra benefits (dental, vision, hearing), and coverage when traveling.
3. What happens if I choose Medicare Advantage now and want to switch to Medigap later, including whether insurers in my state can review my health history or charge more.
4. Key 2027 dates and deadlines.
5. Ten questions I should ask a free SHIP counselor or 1-800-MEDICARE.

Rules: Cite sources for every important claim, preferring Medicare.gov, CMS, my state's insurance department, and independent nonprofits like KFF. Don't rely on insurance company or broker sales pages. If something depends on my state's rules or on specific plans in my area, say so instead of guessing. Write for a smart reader who isn't an insurance expert.

What the AI might say back

Tips

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