If you're even considering Seattle... know that we have white skies (solid) 250 days a year, and if you add 50%-75% overcast over 300 day a year. It's 50 degrees and raining 10 months of the year. Meaning you have to play indoors for all of those 10 months. It's absolutely gorgeous for 6 weeks, but that's it. 2 weeks of winter, 6 weeks of summer, and 10 months of rainy, damp, grey weather. ((I know sooooo many 'transplanters' who think that we just buy our kids $500 worth of raingear every year and play outside in the parks. But we don't. The parks are empty.)) Our weather is "moderate" temp wise, as we almost never hit 90 or freezing... but 50 degrees and raining (which we had all last week) is our "normal" weather. Constant grey and drizzle.
ALSO, cost of living is *through the roof*. New York is more expensive, San Fransisco is neck and neck, and Hawaii is cheaper in most ways.
Average costs:
2b/1ba starter house: 500,000
2b/1ba starter house an hour out of the city: 300,000
Group Daycare for a non-potty trained infant/toddler : $1600 p/month
Preschool: $7000 per year
Private K-6: 15k
Private HS: 20k-35k per year
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I feel ya. I've been looking for "the" place that meets my requirements for happy for a few years now. I want snow in the winter, a backyard pool in the summer, mountains for snow w/in 2 hours drive, beaches for surf w/in 2 hours drive. Small town/village to live in near a train to a big city for culture schtuff on the weekends. Dual Enrollment for school (we homeschool, so K12 districts don't matter... if they DO matter for you, Fairfax County VA has some of the best schools in the nation). For M., I think that's Mass nearish Boston. But Boston is pretty cold/ probably not what you're looking for.
I've lived in Seattle, Huntington Beach (s. of LA, CA), San Diego (CA), Pensacola (FL; aka redneck riviera), New Orleans (LA), Charleston (SC, alligators and humidity), Chicago & Peoria (IL), and travelled to 40 out of 50
Good Luck in your search!!!