Oregon has a lot to see and do. There is a nice assortment of stuff in NE Oregon, near the ID and WA border, but it sounds like you will not have the time for that. I will, therefore, focus on PDX, Central Oregon, and the Coast. I recommend that you buy an Atlas Gazeteer published by DeLorme.
If I were going to be in Oregon, the indispensable drive would be out through the Gorge, you can hit several things like Multnomah Falls and the Bonneville Dam. You can cut off I84 to the south to Hood River and then to Mt. Hood. South and east of Mt. Hood you can pop off of Hwy 26 and take the road to Maupin and drive south on 97. You can fish the Deschutes between there and Bend, or just pull off and check out the river and various trails. Driving down to a place called The Junction about parallel to the turn off 97 to the town of Shaniko. It’s a short and scenic drive to the river and back.
Drive down to Madras, and there you can go back up toward Warm Springs and hit the river at Mecca Flats. Heading south to Redmond, you can pop in on the Crooked River Ranch and fish that portion of the Deschutes (this presumes there is still public access below Steelhead Falls). From there, you could make a short side trip out past Sisters to the Metolious River which is one of the prettiest waters you will ever see. You can drive on down to Bend, south of Redmond on 97, and hit the Deschutes River Brewery, and have a bite and a pint. Hwy 97 south will take you down to Chiloquin, which is were the Williamson River is, and you’ll be there in time for the first “season.” From Chiloquin, you can drive through Ft. Klamath to Crater Lake, NP and check that out. From Crater Lake, you can take the Rogue River Hwy and drive west back toward I-5 and the coast. The Holy Water on the Rogue is a good place to check out and fish,and you may want to check out the Steamboat Inn, which has a lot of history.
From that area, you’d have several choices, and the fishing choices include checking out the McKenzie, Umpqua, and upper reaches/forks of the Willamette. Other scenic choices include Oregon Dunes, NP to the south and east on the coast, or crossing I 5 to the coast and taking the coastal highway north up through Tillamook and on to Astoria.
Portland has a lot of good restaurants. The high end of fine dining is more affordable there than in a lot of cities. Genoa (Italian) and Couvron (French) are at the upper end and cost less than they would in other cities, they were 6-8 courses for $55 and $85 respectively excluding wine but that was a few years back. I particularly liked Esparza’s (great Texmex) in the NE, Pambiche (casual Cuban) in the NE, and Gino’s (casual Italian) in Sellwood. My friends in Portland turned me on to them.