Oahu is always a good island to start off with and it works better since if you have to fly back through Oahu for your return flight, you can work in the connection without an overnight.
I don't think it really matters from there. I would really pick islands based on what flight schedules you can get it on the non-stop flights.
You may also want to create an open-jaw flight to Hawaii (e.g., fly into OGG, depart from HNL and then work in a OGG-KOA-HNL flight in there). That may save one interisland flight from the itinerary.