To me, separating discussion of the Four Seasons and private purchase of property seems appropriate. Wailea is for whatever reason stupid expensive.

The place we stayed at was at the courtesy of friends that don’t and couldn’t rent even if they wanted to. So free place for two weeks and they would have let us stay for month free if I had the time. It’s yet another vacation home for them. Making money on the property isn’t a concern for them, it’s a 4th home.

What shocked me being a West Maui person is how stupid expensive Wailea is relative to Kaanapali. I’d still choose the awesome house I had in a gated community with double the size, 2 car garage, way bigger lanai for less money. I get it, you either like the south end or West end, but is that worth another million?