Downtown has a lot of bland fifty year old buildings. But I like them more than the complicated new ones. But downtown also still has a lot of old buildings.
To be fair, I've been to Portland maybe 3-4 times including a few weeks ago, and this year was the first time I could actually see any of that because it wasn't raining.
You should come visit during summer. June, July, August, and September are typically very sunny and dry, it's a wonderful time of year to be in Portland.
I flew out of PDX all the time around 20 years ago and it was by far the best US airport I went through back then. I'm not sure what you could mean by brutalist hell in terms of portland. There is a ton of green space throughout the city and little if any brutalist architecture.
Are we thinking of the same city? Maybe you're thinking of the one on the other coast? I'm not familiar with it, but the Portland in Oregon doesn't have much of anything brutalist about it.