Wherever you go get there VERY early. During summer, you can’t even find parking anywhere after 9AM. If you’re going from Portland to Bend, take I-84 through The Gorge to Hood River. Then head South on OR35 until you hook back up with US26 at the foot of Mt Hood. Do NOT try to take US26 or you’ll be stuck in traffic lights and crappy urban sprawl for hours, vs. getting to see some of the best scenery, restaurants, museums, waterfalls and save yourself a few hours and a shitload of fuel.
When you head back through to Astoria, you can actually save a bit of time by heading north up I-5 and take WA14 out of Longview. Same stretch of river, but better Mexican food. Clatskanie is a dump, full of speed traps, but Skamokawa is a cute little town. There’s really fuckall to do in Astoria anyway except drink. That’ll put you right onto US101 north. Will take you straight up along the coast-ish near the beaches toward the rainforests. Be sure to get fuel in Aberdeen at the Safeway before you head up the peninsula. Otherwise the Quinaults with take you to the cleaners. Forks sucks, but you can find a cheap motel there if need.

EDIT: I re-read your itinerary, and it is completely wildly unrealistic. The only way you could make this schedule is by doing a bunch of drugs and stay awake for a month straight or own a Star Trek teleporter. Also, Portland has become a shitshow of drug addicts. The main shopping district is a mix of religious crazies and drugged out lunatics.
EDIT2: You’re dealing with an area larger than France, Germany and Spain with almost 0% of the infrastructure. California by itself is larger than Sweden and the 3rd largest economy in the world.