I moved to Seattle in 1990 from So Cal and have basically been here ever since. I love it here and can’t imagine living anywhere else (except for SF about 3-4 months out of the year, but I digress). I’ve travelled throughout the US, Europe, Asia, and the Middle East and bar none, Seattle is the best overall city to live in, IMHO. Here are my observations (thank you OrcaChow for the outline):
Weather: Oct-May are the dreary, cloudy, cold, rainy months. We average 36" of rain each year. Not a lot compared to some cities, but it comes down slowly, like a leaking faucet. More than anything, it’s the cloudiness that gets people down more than the rain. June-Sep are THE best months here in the world!: sunny, mid 70s-low 80s, and occasional “heat” wave (85+) and low humidity. Absolutely perfect, with long days, and hardly any mosquitos! At the peak of summer, it doesn’t get completely dark until after 10pm!
Traffic: OK, it’s bad. My solution, live near your workplace and walk, ride your bike, or take the bus as much as possible. Going across Lake WA (520 or I-90) are risky propositions either direction during rush hour. Yes, it is a natural form of birth/population control, it seems.
And there are really bad drivers here. Three biggest complaints: 1) driving slow in the fast lane, 2) can’t merge properly, 3) indecision at 4-way stops. Kahnnnn!!!
Housing: Recently, the market has been hot hot hot, especially the closer to downtown Seattle you get, but there are bargains to be had. Compared to what you are used to in HI, you shouldn’t be shocked at all. Belltown (just north of downtown) is the up-and-coming urban neighborhood to be in for young, urban, empty-nester types. But the rents/housing costs reflect that as well.
Arts & Entertainment: great live music, dance, and club scene. We are mavens for movies, pubs, coffee houses, and anything else that can be done indoors during the winter. Museums, theatre arts, and sports are metropolitan quality. But I still feel Seattle is a small city trying to be big. That’s why I like it. Most of the amenities of a big city without the big city problems. I lived in SF for a while and, although I think it is one of the world-class cities, it can get tiring at times (crime, crowdedness, cost of living, unfriendliness).
Food: We are in Thai heaven. Basically, any cuisine you want, you can get it. The food is awesome here and so are the restaurants! 'Nuff said.
Bellevue & Redmond (aka The Eastside): Being a city slicker and former So Cal resident, I have a personal bias against all that the Eastside represents. But that is me. It is the bastion of suburbia, families with kids, 3-car garages, empty sidewalks, cultural wasteland, and sprawl. But there are pockets of urbanism developing as the population has increased (e.g., Bellevue, Kirkland, Redmond). People who live in Seattle tend to be younger, single, city slickers, and desire to be closer to the nightlife and cultural riches that are to be had. These are generalizations, but I think fairly represent the different lifestyles you can expect.
Outdoors: You name it, you can do it here, during all times of the year. Skiing is not great unless you drive 4+ hours, but it is OK. Kayaking, hiking, biking, skating, climbing, diving…it’s all here. An outdoors paradise for the active person or those that just appreciate it. This is truly a beautiful place and we have the rain/weather and geography to thank for it. Most people accept and embrace this fact and appreciate what it brings. If you can come to terms with it, you’ll come to think of this as your permanent home. If you can’t, you’ll probably want to leave after three months.
Hatred for Californians: Over-rated. I have not personally experienced or witnessed “hate” crimes against Californians. People in Seattle come from all parts of the US and world and it is actually rare to run into a true native (born and raised). Anybody that razzes you is probably not even from here (total population of WA is about 5.5 million)! In general, the weather keeps us all at a distance at first, which makes us appear cold and indifferent. But behind the facade are generally very nice, socialable people that like to have fun, are conscious of our environment, typically liberal, and like to read, drink a lot of beer and coffee, and hang out with friends. It just takes a little longer to get to know us.
The key to survival in Seattle is a good network of friends and family to survive the dark winters. Hope that helps. Good luck with your move, if you decide to do it. I think you will not regret it.