I grew up in Hilo, live in Honolulu, been to Maui, Molokai, Kauai, hear questions like this from time to time. Let me make some suggestions.
Suggestion Number One: don’t quit your day job, you’re gonna need it. That’s assuming you have a day job. Unemployment on Molokai is probably the highest in the state.
Second, it seems to me that there will be a period of slow times when starting any practice and growing it to the point where it will support two of you, much less allow for buying other than basic necessities. Multiply if there are kids involved.
Third, unless you have significant bucks to tide you over - could be for several years - your best chance to build a business has to be where there’s a market. Molokai’s minimal population suggests it’s one of the last places to start a new business.
Fourth, all the above several times over if you’re haole. Molokai, despite it’s nickname “The Friendly Island” is not so any longer. Downright hostile to certain elements.
Fifth, if you’re not familiar with prices in Hawaii for land, living, groceries, school, and so on, (and even if you are!) you better have a damn good backup/fallback plan. The “Pardise Tax”, that is the premium you pay to live in Hawaii, is about 38 percent, on average. On Molokai it’s higher.
But what the heck, lots of smart, well-educated, capable people get frustrated and leave, just another case of rock fever. Come on over. Bring money.