Living in Seattle on two high incomes(maybe not relative to you, but still) and having no kids was amazing. Paid off about 80k of student loans in a short amount of time. However, the prospect of having a massive 500k-1m mortgage in a boom or bust town was just too much for me. Here, If the housing market flipped upside down and my house magically worth 0$ id still come out alright! It's that, plus I can afford my housing while working at Starbucks(exaggeration) that gives me peace of mind.
I will say though, if Seattle's housing market crashes I'd be back in a heartbeat. I miss the water and the mountains!
Also FWIW my company is remote first, and I get paid the same in Seattle as I do here.
In 2008 it was systemically threatening, I don't see it happening this time. Yet, I'm a little bit like you, I am hoping prices will go down, because I want to buy a condo or 4 unit duplex as an investment and I've been waiting for prices to go down. For years ;-)
In Seattle there doesn't seem to be enough new housing to make prices go down on sale purchases. Unless Amazon goes down I don't see demand lessening. The only thing I see easing is apartment housing. And we need an easing so that people not in "the industry" an afford to live here. Theoretically more apts should lower prices for condos eventually. But it hasn't happened.
As an Amazonian that works remote, I have the same payscale as everyone else in Seattle.