I agree that big island would be the first to chop off the list. It's fine but most things about it are better on other islands. I live part time on Maui and can't speak highly enough about it. I agree with the other post about Kihei/Wailea area. West Maui is just too far isolated to be stationed IMO. Kihei is 15 mins from airport and all the stores. Also, plenty of stores and great restaurants in Kihei.

Wailea borders Kihei and is kind of its affluent suburb - super nice. Shops at Wailea is a great outdoor mall with restaurants, shopping and just walking around. A great day trip is up to the top of Haleakala Volcano - you drive all the way up but can hike around once there. It's the highest point on the island and is like nothing you've ever seen. It's like being in an airplane... but you're not. I've attached a couple pictures.