Excellent summary, Makalani!

The difficulty of housing in Hawaii is compounded by something fairly unusual in the US housing market—seemingly (though not entirely) endless demand.  The gist is that if residents can't buy it, foreign investors will.  That makes it very hard, like a Scylla and Charybdis with the more extreme risks of a worse housing shortage, or overbuilding and having communities choked with units that are more often than not empty, and AirBNB's.  

That Native Hawaiians have to live at the furthest reaches of the transportation network, and experience the most disproportionate impacts of our development system, to facilitate vacations, is salt in the wound.