To paraphrase M. Stanton Evans...
"Hawaiian islands are like sex; when they are good, they are very, very good. And when they are bad, they are still pretty good."
What Devert said. We have a house on the *th (security reasons )Fairway of Waikele GC in Oahu which also happens to be next to the Outlet mall. Jim's is by Hawaii Prince GC. My favorite outer island destination with the kids is Maui particularly the Wailea area. When it's a romantic getaway with the wifey, it's Kauai where we honeymooned (Princeville). For Golf it's Maui again by a mile. The Kapalua complex gives you many different looks. Oahu courses are a bit generic with the exception of the Links at Turtle Bay near the North Shore and the much too difficult Ko'olau on the slopes of the Ko'olau range.
As I go for Golf, shopping and foodie-ing my favorite months are the cooler months.
I've yet to visit Lanai or Molokai. I'd love to some time. When I want to get off the grid typically I do that here in the Philippines. I go to either Amanpulo or one of the resorts in the Coron chain in Palawan. I'm trying to see if I can carve out some time next year to stay in Wailea again. Kapalua is just too far from everything else. Where in Maui do you live?
We honeymooned on Maui in 1967 at a small resort with grass thatched cottages. 99% of what you see today on Maui hadn't been built yet. The changes, on all the islands, are sad. Native Hawaiians no longer own their lands. The song "Waimanalo Blues" (covered by many Hawaiian artists) says it well.
In 1979-80, we sailed from Bora Bora, Tahiti, to to Hilo on our 40' ketch, and then spent 6 months working our way through the islands to Kauai which is still today my favorite. For many pleasant weeks we were anchored near the beach in Hanalei Bay, before setting sail for San Francisco, completing our 2 year odyssey.
It is very sad, but I don't think native Hawaiians have owned their land since the early 20th century or even earlier. One of the most disgraceful episodes in US history IMHO.