I'm sure you must have checked this out, but I thought the waiting lists for a slip in Hawaii were years long. I don't think you can stay in a transient slip that long. If the waiting lists are as long as I think they are, one work around would be to buy a boat with a slip.
Well, I called Ko'olina Marina in Hawaii. I am going to get on their waiting list for a liveaboard slip so we'll see how that goes. I think I am going to live in the transient slips in the Ala Wai (Waikiki) for 6 months and make the move to Ko'olina when my number comes up on the waiting list.
As for the house... I am going to hold off on making that decision until we move stateside (in about 3 years). In the mean time we are going to take the advice of the majority here and make our lives what we want them to be without regard to "the program".