Seattle is challenging. I want to say that there is still lots of room for its prices to go up, because we're nowhere close to San Francisco or Vancouver. It's a desirable place with clean air, abundant water, poor public transit options, and not much room to build, so I think the close-in neighborhoods will appreciate a lot. Then again, it's a city of boom and busts and it's been going up really quickly, so it's hard to tell.
We are closing on our first home in NE Seattle, a solidly built 3 br/1 ba midcentury house in a walkable/bikeable neighborhood 3 miles from the University, where my husband is a professor. We have a baby on the way and plan to stay for 7, 10 or even 20 years. It has a detached shop that we could convert to a rental cottage (expensive but would be worth it).
Over the past two years, we have uncomfortably watched while prices climbed, then skyrocketed, in our area. We are below the median income of 130k but had substantial savings. We ran a lot of calculations, agonized, got outbid, looked at neighborhoods we didn't really like, saved more money, then got really stubborn about staying in our neighborhood. This year, in addition to the general stock market runup, we had some good luck with single stocks (I love me my index funds, and they make up most of our portfolio but that luck was much appreciated)...
Ultimately, because of our long-term outlook, life changes, and repeated steep rent hikes, we decided to stop trying to time/analyze the market and buy.
The house will be a place to live, update over time, raise a family, and practice hospitality. When we do sell in the far future, it will at least have been a good hedge against inflation and a way to accumulate wealth slowly. Bonus if we make more money than expected on it.