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The JCKC Notebook.

Plain-English guides to tax, ACA, life insurance, Medicare, notary services — and the financial questions South Florida families actually ask.

A Medicare member sorting their prescriptions into a weekly pill organizer at home
Medicare

The Cheapest Medicare Drug Plan Is Usually the Most Expensive One

Every autumn people pick a Medicare drug plan by sorting the list by monthly premium and taking the cheapest one. It is the single most expensive habit in Medicare. A plan’s premium is a small, fixed number; what your drugs cost under it is a large, variable one, and the second number is the one that decides your year. Here is how to compare plans on the thing that actually matters, with the 2027 figures and the traps that make a “covered” drug cost you anyway.

September 24, 202612 min read
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A retired couple at home reading their Medicare plan paperwork together before Annual Enrollment
Medicare

Medicare Advantage or Medigap? In Florida, One of These Doors Locks Behind You

Annual Enrollment is sold as the season when everything is changeable. For one decision, that is not quite true. You can move from Medicare Advantage back to Original Medicare any autumn you like — but no federal rule says a Medigap insurer has to sell you a supplement once your first six months are behind you, and Florida adds no rule of its own. Here is how the two paths really differ, where the one-way door is, and which exits exist.

September 21, 202613 min read
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A storm system moving in over the water off the South Florida coast
Medicare

If a Storm Made You Miss an Enrollment Deadline, You May Still Have Four Months

There is a rule almost nobody mentions until it is too late: when FEMA declares an emergency or a major disaster for your county, people who missed an enrollment deadline because of it can get another chance. Medicare gives four months from the start of the incident. The Marketplace gives 60 days from the end of it. But the rule is narrower than it sounds, and the detail that surprises people most is that you do not have to live in the disaster area to use it.

September 17, 202613 min read
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A family reviewing health insurance paperwork with an advisor at a desk
ACA / Obamacare

The 2027 Marketplace Deadline You Have Probably Read Is Wrong — Here Is What Actually Applies in Florida

Most of what you will read this month about the 2027 Marketplace deadline is based on a rule a federal court struck down in June. Here is what a July 2026 CMS statement actually says about your enrollment window, the subsidy rule that no longer applies, and the one change that did survive and makes your income estimate matter more than ever.

September 7, 202616 min read
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