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I'd echo what in_my_travels said about the monotony of a tropical climate, it's nice that you can "escape" with the volcanoes and higher altitude locations but that's a temporary kind of fix. Both are two of the most scenic states in the US with considerable differences from one another so you're aren't going to suffer too much from a scenery standpoint.
Why don't you look at an island that's also in the Pacific that could be the prettiest place on the planet with similar weather to portions of Oregon. I'm talking about New Zealand! I'm kidding... or am I?(I am but not about the prettiest part of course...)
neat thread OP, im in similiar boat in terms of consdiering where to go. Im going to be visiting Oahu soon and very strongly considering stopping by Portland too. For me, Cali has always been my second choice behind Hawaii. I absolutely love California as a state especially San Diego and San Fran. however as MuffinMan18 just said...New Zealand is amazing.
im in Wellington and have been living in NZ for the past year and i wish i could stay. if one loves outdoors then this is on one of the best places in the world for it. However, Ecuador has similar vistas, as does Chile, Nepal, Alaska....etc. Anyways in terms of laid-back atmosphere, relaxed population, safe living, NZ is absolutely amazing. You might want to look into BUNAC - they offer i believe 2 different working holiday visas 18-30 and 18-35 for NZ. that second one is unique to NZ. you never mentioned travel in your ideas however at your age, this would be perfect time to go do some working holiday visas...couple European countries, Australia, NZ....
and a connection between Hawaii & NZ is both have Polynesians, in NZ they're Maori.
Many of your questions can be answered by a book called The Real Hawaii Life, True Stories of Relocations to Hawaii by Kat Varano. It is full of stories and interviews and lots of pictures of people who have moved. It has a lot of reality, which includes good and bad.
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