If you are considering Portland and Mt. Hood, you might look at Vancouver, WA, on the north banks of the Columbia River. Voter maps may show it as red because of previous presidential elections but overall it's pretty equally balanced, and Vancouver itself leans largely progressive. Washington's US senators, our region's US Congressional rep, and the majority of our state legislators are all .
Yes Oregon has no sales tax, while Washington does, but Oregon income tax is very high. Consider that every dollar you earn in Oregon is taxed, but not every dollar you spend in Washington is taxed. I will say that Washington has one of the highest gas taxes in the nation and I often will gas up when I'm in Portland to save $0.20 per gallon.
I bought a home in Vancouver 30 years ago and got more house for my money, lower property taxes, better schools, and better social services. I think housing is still more affordable in Vancouver vs. Portland. The entire area has many amenities important to me: great grocery and pet supply options, world class medical care (both traditional and alternative), lots of history, great museums and parks, a vibrant restaurant scene, excellent higher education institutions, plenty of outdoor activity options, proximity to the ocean, and gorgeous scenery.
Downsides: It's a little further than your stated parameters. I live just north of downtown Vancouver, west of I-5, and can be to Timberline ski area at Mt Hood in about 1:30 - 1:45. Wildfires are definitely a concern and we're all learning to live in the new climate reality. Traffic can suck at certain times of day, but it's still better than Seattle imho. And of course the rain lol. But this area has fewer gray days than the Puget Sound region, and warmer summers too.
Good luck in your search!