I'm a longtime member at Pumpkin Ridge, and live on the west side of Portland.
1. It's a lot less crowded than Seattle. Seattle is geographically constrained, but by some wonderful features. The Puget Sound is the calmest body of water I've ever seen, glassy smooth at times. Mt. Rainier is big, but not as pretty as Mt. Hood, and especially Mt. Shasta.
2. In Portland, there are some congested highway corridors; especially the two arteries (I-5 and I-205) between Portland and Washington state. In general, especially given our low maximum speed limits, traffic is exceptionally polite and well behaved. A very mellow place to get from point A to B.
3. Mt. Hood and Mt. St. Helens are visible on most clear days from some parts of the city.
4. Pumpkin Ridge has the most pristine and beautiful location. The western half of the Tualatin Valley is colorful, agricultural land that Washington County designates as untouchable. The golf courses have a straightforward, championship style design, and both courses are still in most publication's top 250 in the country. What is underreported is the great "maintenance meld". Once it dried out, it played fast and firm and perfect this year. In late June, I hit a 3-wood on flat ground with a 5 mph downbreeze that bounded the last 60-70 yards onto the green. The ball bounces around here, and there are shotmaking opportunities.
5. The downside to living on the west side is airport proximity. 30-40 miles, 35-45 minute drive during offhours, perhaps 50-80 minutes in traffic. But if he can arrange his schedule, the highways are open most of the time.
6. If I were shopping for a golf club membership other than Pumpkin Ridge, and planning on settling down for years, I might head to Waverly Country Club and inquire. It's on the east side, right on the Willamette. It's only about 6600 yards, with some enormous specimen trees. A few of the greens are too sloped. All it needs is a little fixing up, and it will be the best one. Good land, great location and a good routing.
7. Of course, if it's that fancy, shmancy metropolitan glitter you're after...