This is an interesting post.... I am wondering if anyone that has lived in any location since 1965, would not care for the changes that have taken place since then. I am sure that they could say almost the same things as you said regardless of location... I think real estate is expensive anywhere that is desirable to live. (I am sure that you could find cheap real estate in areas such as rural Nebraska or Kansas or other areas that are not 'hot areas' to live in).
If you think the winters in Oregon are tough, try Minnesota where I live. (Our solution is not to move permanently, but only to leave during the winter). Also Minnesota's Taxes are higher than Oregon overall Minnesota is #5 and Oregon is #30 --
https://wallethub.com/edu/states-with-highest-lowest-tax-burden/20494/ ----
We're not leaving Minnesota in spite of the Weather, The Taxes etc.... Mostly because other places have different problems. South Florida has Nice weather, but has other issues etc.
The question I have for you, is where will you move to and have you examined that destination's problems? -