One tact is to live where you are now, as "if" in Hawaii. Live listening to a given type music radio station, such as at this link on local radio; "on line" :
Radio Stations in Honolulu - Listen Live Online Radio
Oldies at 107.9 may be selected , for example. Also, live daily in 500 sq feet for 6 months, even if your home is much larger. Set aside the extra money as "if" paid, for a space IN Hawaii; same for food costs, electricity, and all routine costs. In other words, spend by NOT accessing the extra money and leave it "aside". These ONLY are practical NEEDS, and may have more per individual. Climate and lifestyle IN Hawaii are not the point, but, only to determine ability and happiness of "cost" to live there. Make a list of YOUR annoyances from noise, congestion driving, shopping and taking the food etc home on a bus or not-taxi? or, just going out to a venue. Carrying these 'to" your residence, ie condo, etc. and effort/time/hassle for YOU or not. Pay yourself extra "aside" for a monthly covered/UNcovered parking space at home or, any place you may go elsewhere, for 1-4 hours. These are suggestions and must be tailored to each person or family.
Point: Walk the walk BEFORE having to do so. Relative sick in the mainland? Need to go? Set aside air fare and consider it gone. Living vicariously consists of the BAD along with, the GOOD. Again, all the wonderful "paradise" concepts are the "extras" for which you MAY accept practical realities to live anywhere, and, unique Hawaii.
Just a thought...
PS- schools? land area? interactions with people?
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