I moved out of San Francisco to Maui about 15 years ago. Loved all the energy, great food. music, etc of S.F. but after the surge of dot.com mob came in it was to crowded and expensive. Maui was and still is a major deal in comparison. I would probably have to pay nearly 15X to get a comparable place in S.F..
Why Maui and not Kauai or the Big Island? Spent plenty of time on all the islands including have lived in Kailua/Oahu for many years. Native Hawaiian's call Maui nō ka ʻoi which means "Maui is the best". Most mainland transplants like Maui the most as far as living here. For sight seeing I think the Big Island is the best. Kauai is where honey moaners go - not to much there although it is nice to visit. Big Island - Is rugged jungle living - it is not so Haole (non-local) friendly. Maui - Is considered the best by international travelers. It is the world mecca for kite & wind surfing, which is my reason for being here.
In early 2000s I had noticed quite a few NorCal 1%ers buying vacation homes on the Big Island and on HGtv series "Hawaii Life" it seems most moving to Hawaii from the mainland are either going to Oahu ( job transfer) or the Big Island.
The Big Island has the lowest land/home prices but there is a reason why it is cheap. Most transplants don't last more than 2 years than move- many people I knew that tried to live on the islands ended up moving to Florida and like it a lot - I was in Naples, Fl. recently - nice.
Jobs are on Oahu but living there sucked far worse than any of the 20 odd places I've lived in my life. I agree Maui is the best balance of having the stuff you need to live day to day life and not dealing with the garbage dumping, grafitti, meth encampments on the beaches, traffic, crime.... of Oahu. Big Island would be second and Kauai a beautiful but very rural third. Couldn't pay me enough to move back to Oahu.
What's not to like about Naples, I've come across many retired Europeans there especially Swiss. I have been both to Oahu and Maui, to me rural nature of Kauai seems the most attractive ( on paper of-course).