The primary reason Jay is there is because its very far from any population center (and he loves to swim in the ocean).

It may be quixotic which places might do better/worse post peak - for example, many think New Zealand will be a disaster due to the fact that the oil tankers will just not go past Tasmanian Sea if they have no Forex to pay. But that may be a blessing - for those that are prepared ahead of time, New Zealand will be left alone, and forced to change a bit before the rest of industrialized world will - cold turkey rather than leftovers for a while.

Post peak perfect spot does not exist. Its a dynamic tradeoff between: low heating/cooling days, water, agriculture, low population density, high friends/community density, beauty, healthy ecosystems, out of fall-out paths, local fuel sources, etc etc. My gut tells me the 'friends/community' will be the most important part. (but then again, my gut told me to eat a pizza at midnight last night...;)

He'd probably be better off picking a different island.  The older islands are more fertile, and have more water.  

By the time Hawaii was "discovered" by Capt. Cook, the Big Island had already reached its Malthusian limit, or was close to it.  There's a reason King Kamehameha arose there, to conquer all the other islands.  This article argues that it was food shortages that drove the conquest.  

It's estimated the Big Island had a population of about 80,000 when Cook landed.  That's less than half the population today.

I fancy Iceland's chances myself, but I don't speak Icelandic so I don't think my prospects there would have amounted to much even if they let me in, which I doubt they would have. Shame. I don't mind the cold - excess heat is far worse as far as I'm concerned.
I am quite happy about living in Sweden. Low population, lots of biomass, lots of hydropower, lots of nuclear power, high technology, ok environmnet, ok infrastructure, a tradition for cooperation, fairly well functioning state even if it could be much better. Although we or rather the greens and the aged socialist party made a clusterfuck out of our military and our civil defence after the cold war ended.

I use to half as a joke and halfway serious say that if we took the liberal parts of our state and laws and applied them on the rest we could get americans to move over here in 10 years.

My personal Peak Oil or other disaster planning is to try get more friends, but I spend too much time on-line, someday build a summer cottage on my fathers farm, start to work in the energy business and as a hobby become a small functioning part of our government on a practical and a political level.