I lived and worked in Portland from 2012-2018. Moved there from the DC area.
I skied Mt Hood Meadows 2 or 3 times before I started driving to Bachelor instead.
The first time, the primary part of Meadows was pretty icy. I was advised by a young man that it wasn't really suitable for an intermediate skier who doesn't know the mountain. So I skied the green trails off to the left and worked on skills.
When I did get to the main body of Meadows on another day, I couldn't tell much about where I was. All I could think was "why don't you put some money into some damn SIGNS". I am very comfortable with ski maps, but I couldn't find signs to match up to the map.
It may have been 1.25 hours from home (near PDX airport) to Mt Hood, but it took that long just to get off the mountain on a weekend. Drive home was close to 3 hours.
Then a friend told me that Meadows has ditches or gullies or something that I should be cautious of. I dubbed Meadows a "locals mountain" since apparently you have to already know the place to ski it safely solo.
I skied Timberline a few times, but only midweek or late season, and really enjoyed it.
I did more skiing when I lived in the DC area than in Portland. And skied Bachelor more than Mt Hood.
I'm sure there are others on here who know way more about Mt Hood than I do and who like it. It was just a PITA to me.
During my last full year in Portland, a radio announcer informed us that that was the 300th consecutive day without sun. IIRC, Portland actually gets more rain than Seattle.
Vancouver, WA may offer the best of both worlds wrt taxes. No income tax and you can cross the river to shop tax-free in Oregon.
Seattle had more of a city feel to me, so Portland might seem friendlier. But I was never convinced it was actually true.
To me, in DC, if someone doesn't like you and sees you coming down the street, they'll probably avoid you. In Portland, it felt like if they didn't like you, were on the other side of the street and saw you coming, they'd cross the street to stop you and chat with you, then talk about you behind your back. I had been forewarned that the Northwest has a reputation for passive-aggressive behavior. Since you're in that region, you may be used to it. I was not.
OTOH, Portland is full of locally-owned restaurants. I'm a picky eater, so exploring them felt risky! But I felt welcome and appreciated. My current location is south of Denver ... and this is the mecca of chain restaurants. That's one of the things I do miss about Portland. But you may find more of a chain restaurant culture in the family-friendlier areas around Portland, so YMMV. And you may find the people to be very accepting of newcomers.
Charts from Wikipedia:
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Blue areas are more populated so the state may lean that way, but that doesn't mean you'll encounter blue attitudes everywhere you go
I didn't spend any time in Tigard, but based on the people I knew who lived there, it did seem to be family-oriented. Beaverton and Lake Oswego also seemed popular with families.
I'm not trying to argue your pros and cons, but my experience differs from how you're seeing it. There may be a whole host of reasons why Portland is the right place for you. And your priorities will be different than mine. I met many people there who were born and raised in Portland who cannot imagine ever living somewhere else.
There were pockets of people and places in the Portland area that I really enjoyed and that I miss. But I had retired and Portland seemed to be declining, so I decided it was time to move on.
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