Awesome plans Craig, love the Sunburst idea, that's a ripper and having lived in the Island for a long while I can see them enjoying that a lot, be they sailing or just watching.
Agree on maintenance, that is not a strong point on most islands, which is rather strange when you see most Islanders must be where they got the idea for McGyver from. I've seen them make some awesome stuff out of bugger all. The Kiribati racing Proas for example. When I was up there they discovered a new high tech material that made the boats that much faster, a bit like the AC found foils. In Kiribati they discovered the plastic sheet used under concrete slabs laminated using a glue made from palm sap between their more traditional cloth, a blend of cotton bed sheets and a cloth made from the fibres of coconut palms, was a big performance gain. Funnily enough those boats do over 30kts and those sails are the highest tech thing on them.
Or I saw a lady one Sunday heading off to church in Tuvalu, a very religious country, wearing an spectacular hand made very intricate dress in wickedly shiny red/white and polished alloy. It was fully made from used Coke cans flattened out then very tidily sewn/lashed together. I hate to think what would have happened if she slipped over or sat down wrong, I suspect it would put a whole new meaning on 'sliced n diced'.
Anyway, any maintenance skills they can get can only be a big bonus, especially to some of the outer communities.
What you need is a tall friendly bald dude who may own something like say a 60fter, a sleak black one could be nice. I'd think it would have lots of deck space for dingys and maybe even an owner chomping at the bit to get the F out of this place we don't call Dodge so possibly ready to jump at any excuse. I wonder where someone like that maybe lurking