Agree with @Vegas_Millennial about arriving one to two days prior to the tour start. Jet lag, missed connections and lost luggage can make your planned trip hell.
Yes to travel insurance - cancellation as well as medical emergency. With regards to amount of clothing, depends on the tour. Are you in the same hotel for the duration, or are you moving in-between islands? If the former pack as much as you want, if the latter pack light and use laundry services. See If the tour company does everything, loading/unloading luggage into transport, Airport transfers, and getting it to your room, helps curb urge to overpack since you’ll be doing the work. Pack your bag several days before the flight then two days prior go thru it and remove 1/2 of the stuff. Personally I try to pack light.
given the flight times 16 - to 20 (from the US) hours plus connections, I’d use the points and go business class. Flying to Australia from the east coast I never regretted booking business class on those flights.
have fun!
Similar to @Wanderoz I found him better looking than his posted pictures, same comments on the body. Had a session late last year at his Maryland location. He was very friendly and skilled; session was more a combo therapeutic/sensual massage. I'd book another session with him if our paths cross.
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