Long term anchorages or moorings on Maui are pretty much non-existent. There are no marinas on the island, and only two small-boat harbors. The few slips available to private owners have a many-year waiting list. There is a mooring field off Lahaina, and I am told you can dive and put in your own mooring, and pay an annual fee. You might need to go on-line and check up on that, though. Somebody else said that anchoring is not allowed here (Maui). Whether that is to protect the coral, or because of the Humpback Whale Sancuary, I don't know.
Many people here go with trailable boats. I'm in the market for a day-sailor I'll keep near the condo.
I understand Oahu has marinas and quite a few live-aboards. That might be your best bet. Best of luck on your future in Paradise!