There was a DO out sailing with his wife when we were cruising. They didn't have to worry where there food
was coming from and his wife seldom had to cook as they were always invited to someone's house for dinner. Maybe not a 6 figure income
but volunteer labor and occasional real dollars from other cruisers could have kept them cruising forever. There were clinics on the bigger islands but mostly manned by paramedic level help. On the smaller islands, it was a long boat ride to get anything more than bandaids and asprin. You won't get rich but you won't starve either.