There are so few doctors (specialists, in particular) on all of the islands combined that it would be fairly easy to determine exactly who you are talking about. It is nothing like the mainland in this respect.
If I were you, I would suggest shopping for schools before falling in love with any particular town or island.
I have had many friends move to an area, only to find out that the local public school ranked in the bottom percentage of ALL US schools. The better private schools usually have LONG waiting lists and very difficult entrance exams.
BTW, now is a terrible time to buy in Hawaii. Although their market tends to lag behind mainland trends by a year or so, things appear to be shaking up a bit already. Hawaii is no stranger to housing bubbles. We were hit HARD by the burst of the Japanese RE/investment bubble. People were upside down in their mortgages for 10-12 years. These are people who once had a lot of equity…
Hawaii is a fabulous place to live, but there are a few dark alleys in this tropical paradise, if ya know what I mean. 🙂