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March 18, 2026 26 mins

Navigating Medicare can feel overwhelming, but it doesn't have to be. In this episode, Meg welcomes Corey Dobashi, a Medicare broker and retirement specialist with Milestone Wealth Management based on Kauai, to break down everything you need to know before your 65th birthday. Corey walks through the three main Medicare options — original Medicare, supplemental plans, and Medicare Advantage — and explains how to choose the right coverage based on your health history, medications, and budget.

Corey brings over a decade of experience helping kupuna across Hawaii and the mainland navigate their retirement healthcare decisions. He also touches on the gaps Medicare doesn't cover, including long-term care, and why working with a broker early can prevent costly, permanent penalties.

The bottom line? Love your broker — and start the conversation before you need to.

In this episode, you will hear:

  • What is the difference between Medicare Part A and Part B — and why does it matter?
  • The three Medicare plan options and how to choose the right one for your needs
  • Why Medicare Advantage plans are growing in popularity in Hawaii
  • How your current medications should influence your Medicare plan selection
  • What happens if you don't enroll in Medicare Part B or a drug plan on time
  • Why long-term care isn't covered by Medicare — and what to do about it
  • The value of building a strong relationship with your Medicare broker before you need one

Resources from this Episode

Corey's Website - https://www.milestonewealthhi.com/

Corey's Contact Number - 808-778-0377

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