What Should Tutu Choose for Medicare?

A Simple Guide for Hawai’i Families

Turning 65 comes with a big milestone: Medicare. For many families in Hawaiʻi, helping Tutu navigate her options can feel confusing—but with the right guidance, it doesn’t have to be.

In our recent conversation, Medicare broker and retirement specialist Corey Dobashi of Milestone Wealth Management breaks it down in a way that actually makes sense.

First, it’s important to understand the basics. Medicare is split into different parts—most notably Part A (hospital coverage) and Part B (medical coverage). While many people qualify for Part A automatically, enrolling in Part B at the right time is critical. Missing that window can lead to lifelong penalties.

From there, Tutu has three main paths to choose from:

• Original Medicare (Parts A & B)
• Supplemental (Medigap) plans to help cover out-of-pocket costs
• Medicare Advantage plans, which bundle coverage and are becoming increasingly
  popular in Hawaiʻi

So how do you choose?

Corey emphasizes that it all comes down to personal factors—especially health history, current
medications, and budget. For example, certain prescriptions may only be covered under specific
plans, making it essential to review drug coverage before enrolling.

Another key takeaway: Medicare doesn’t cover everything. Long-term care—like extended
nursing home stays or in-home care—is not included, which can catch families off guard if
they haven’t planned ahead.

Perhaps the most important advice? Start early and work with a trusted broker. Building that
relationship before you need care can help you avoid costly mistakes and ensure Tutu gets the
coverage that truly fits her needs.

At the end of the day, Medicare decisions aren’t just about paperwork—they’re about peace of
mind for the whole ʻohana.

Resources from this Episode

Corey’s Website – https://www.milestonewealthhi.com
Corey’s Contact Number – 808-778-0377