I recommend you spend a week or two visiting the various islands. Each island is different and has a different vibe. Spending a few days on each island should give you a good idea of the lifestyle and people. There is a labor shortage on the islands like many parts of the country and opportunities are bountiful. The prices are not that crazy and compared to San Fran-may be a bargain. I have family that lives on Maui and on Big Island Kona coast.

A website that I check out every so often will give you a look at the Maui real estate market. Browse under Listings By Area. While you are there-click on Beach Cam and check out the live Charley Young beach cam...

https://www.mauirealestate.net/

Oahu I call the concrete island. Maui is magical but it also revolves heavily around the tourism industry. The Big Island is huge and has several different climates and topographies to choose from. If I were to look I would check out Pukalani, Kula, Makawao, and Kihei on Maui. Then I would check out Kona on Big Island. You only live once and life is short-if you want a change of attitude and latitude Hawaii is a great place to start.