I just moved to WA State a couple years ago after living in Oahu for 12 years (Kaneohe then Ewa Beach - the Tagaviolas lived a few blocks away).
Never spent any time in Mt Angel or Oregon City. Ive been to Gresham, but way back in the 1990s. All of Portland and the burbs seem like they are on a different planet now.
As with any big city, you can find places with lots of space but the commute is probably going to suck.
One idea to consider is living on the WA side of the border. A bunch of my friends live in Vancouver, WA (just north of Portland) and commute to Portland.
I think you mentioned Lake Oswego, that was where the rich folk lived. So I'm guessing it's still pretty nice. Btw, a number of those high schools in Portland with good sports like Jesuit and Central Catholic are private. So be prepared to pay a college tuition if you send your kids there.
A decent area with good quality of life is Hillsboro. Not sure about the HS there. West Linn is a nice area and as discussed, has a HS with good sports. And it's a public school, so thats a bonus.
Oregon is a great place to live, especially if you live in a red part of the state (basically everywhere else in Oregon outside of Portland and Eugene).