From Diane

Insights

Monthly newsletters, Maui market updates, and weekly videos: everything I share with clients about living, buying, and selling on Maui, in one place.

The Hidden Costs of Owning a Home on Maui (It Is Not What You Think)

Video

July 31, 2026

The Hidden Costs of Owning a Home on Maui (It Is Not What You Think)

Hawaii has the lowest base homeowners insurance in the country, and that one fact has misled more Maui buyers than almost anything else. After more than a decade in this market, here are the ownership costs that show up after closing, not before, and how to budget for the real monthly number.

Maui's New Short-Term Rental Law, Explained: What Bill 9 Actually Changes

Video

July 24, 2026

Maui's New Short-Term Rental Law, Explained: What Bill 9 Actually Changes

Maui just ended vacation rentals for roughly 6,200 condos, and the headlines say it either kills the market or gets thrown out in court. After more than a decade selling here, I think both takes are wrong. Here is exactly which properties Bill 9 touches, which ones it does not, and the deadline clock that is already running.

Newsletter

July 17, 2026

An Update From Maui: July 2026

June's numbers are in and they tell two very different stories, plus Bill 88 becomes law and the first rezoning resolutions start moving.

The Four Hard Parts of Retiring on Maui Nobody Warns You About

Video

July 17, 2026

The Four Hard Parts of Retiring on Maui Nobody Warns You About

The hard part of retiring on Maui is rarely affording the house. It is the monthly costs that compound, the island's smallness, real limits on healthcare access, and community that takes years to earn. After more than a decade here, I break down all four.

The Maui Real Estate Market Is Splitting in Two

Video

July 10, 2026

The Maui Real Estate Market Is Splitting in Two

There isn't one Maui market right now: there are two, moving in opposite directions. I walk through the soft condo side, the active single-family side, and where Bill 9 fits in, so you know which market you're actually shopping in.

The Unexpected Pros and Cons of Retiring on Maui

Video

July 3, 2026

The Unexpected Pros and Cons of Retiring on Maui

The median home on Maui is around $1.3 million, but the price isn't what makes most people second-guess the decision later. After 11 years here, I lay out the real pros and cons of owning on Maui so you can go in with both eyes open.

Video

June 26, 2026

NEVER Buy These Types of Homes on Maui

After 11 years on Maui I've watched buyers get blindsided by the same five property traps over and over. By the time most people find out, they've already signed. Here's what to look for before you close.

Where to Retire on Maui: The Four Lifestyles Compared

Video

June 19, 2026

Where to Retire on Maui: The Four Lifestyles Compared

The best place to retire on Maui depends on which trade-offs you can live with: Kapalua for understated quiet, Wailea for resort amenities, Upcountry for land and cooler air, and for some buyers, a different island entirely. After 11 years here, I compare all four side by side.