Sailing from the West Coast to Hawaii
Check with the Hawaii and Waikiki Yacht Clubs they have a list of guys looking to crew these sorts of trips. I had a friend who did it frequently.
There are a couple of new marinas on the leeward side that are pretty good. If you or your wife are military or civil service there are a couple more options available.
I am surprised that it is cheaper to sail rather than ship it to Hawaii but it would certainly be an adventure.
Start watching Hawaii 5-0 to pick up on the local pronunciations like Likelike, Kamehameha, and Kalanianaole the old 5-0 not the new one. You be speaking like a kamaaina in no time.
There will be a significant culture shock for your son and schools vary significantly from one to another that would determine where on the island you want to live. There are places on the island I would not mind living but would not want that environment for my kids.