I don't live in Portland. I live about 4 hours south of the city on the Oregon coast, but I get up to Portland enough to recommend things at, maybe, a level 7 (turns confidently both ways on main streets, merges smoothly at rush hour, knows the major landmarks and annual events, etc.) I also lived in PG and Montgomery counties in a different lifetime while going to school in Maryland, so I know that part of the world a little also. I'm pretty sure you will never look back once you settle in.
In general terms: Portland does not disappoint. There is great coffee, wonderful beer, good ethnic food, excellent music, ready access to all sorts of recreation, and a whole lot of people who get around on bicycles. The cold, rainy winters can suck...but then again, cold rain in the city means snow at Mt. Hood Meadows, Mt Bachelor. etc.). The summers are glorious.
I can recommend a few things that I like to do as a semi-tourist: going to Trek in the Park, being there on the day when cyclists take over the city bridges, walking around on 23rd ave or SE Hawthorne Blvd. There’s a good Saturday market downtown, another pretty good farmer’s market out in Beaverton on Wednesdays and Saturdays, and those are just the ones I know about.
You may also want to check out The Grotto. It's out near the airport, not far from the intersection of I-205 and I-84, It's a Catholic Shrine, but much more than that, it is a safe and beautiful natural sanctuary.
Southeast out of Portland is the neat little town of Silverton; and southwest out of Portland is a mini-Napa valley in Yamhill County. Check out Carlton, which has about 2000 people and about 40 wineries,
You definitely want to spend a long day in the Columbia River Gorge, driving, hiking, looking at big sturgeon at the Bonneville fish hatchery, and maybe ending up in Hood River, which is a great little ski/windsurf town.
If you keep going east -- way east -- you'll end up in Pendleton. Lots of snap-button shirts and Levi 501s in the thrift stores, a famous rodeo, not to mention the Pendleton Woolen Mill. Most Pendleton clothes, blankets, etc are made in China and Malaysia, but they still do some token blanket-making in the original mill in Pendleton.
Other interesting places to visit in northeast Oregon include Baker City (check out the Geiser Grand hotel and the Oregon Trail Interpretive Center), and further west, Joseph, which is nestled up against the Wallowa mountains and just a short, beautiful drive from the Oregon side of Hells Canyon. If you are ever out that way in the winter, Anthony Lakes is a fun little ski area halfway between Baker City and La Grande.
Headed back towards north-central Oregon, there is some beautiful high desert country northwest of John Day. Also in that part of the state is Prairie City and the Strawberry Mountain wilderness area if you want a remote wilderness experience.
Bend is the vortex of central Oregon. It used to be a small town, now it’s a small city. Ski shops, coffee shops, bike shops, flyfishing shops, trout streams, restaurants, EpicSki supporters, Mt. Bachelor...Bend has it all. If you like trees, the old-growth ponderosa pine forests in and around Sunriver, Bend, Sisters, and Camp Sherman are as beautiful as any I’ve ever seen. If you do make it over to this part of Oregon, check out Camp Sherman and the Metolius River, Sisters, Sunriver, and maybe Paulina Lake...and Maupin, which is a funky little river-rafting town north along the Deschutes River.
Further south and east of here, you get into what is charitably called Oregon’s outback. Miles and miles of nothing but miles and miles. It is spare and, in many places, starkly beautiful country. There are isolated mountain ranges, rivers, and quirky destinations all through here – Frenchglen near the southwest end of Steens Mountain, the Chewaucan river above Paisley, Summer Lake and Winter Ridge, Summer Lake hot springs, the Cowboy Dinner Tree near Silver Lake.
Further west, you get back into the Cascade mountains. In this south-central part of the state is Crater Lake, Mount Bailey, the North Umpqua River, and, further west, the wine country west of Roseburg along the main stem of the Umpqua. Then there’s Ashland, Jacksonville, Eugene, the beautiful coast between Port Orford and Brookings, the equally beautiful coast between Florence and Yachats, and on and on it goes. There’s a lot to do and see here!