I have a feeling a lot of people will pick Portland so do your first and second (and last) choice please.
Portland: The quirkiest major city in America, home of hipsters, the Blazers, antifa, and gentrification. I don't think this one needs too much explanation. Most of the city is your typical urban environment. The downtown is on the west side of the river but besides that the west side is your richer area and it's full of hills compared to the flat eastside. If you like urban environments this is your only choice.
Portland Suburbs: Want the big-metro feel with slightly lighter traffic and more space? There are plenty of places to pick from. Gresham, Beaverton, Hillsboro, Tualatin, Tigard, Lake No Negro Lake Oswego, Clackamas, Oregon City. There's a lot of variation. Some have plenty of character but some are generic and soulless. Washington County's become a tech hub with Intel and Tektronix and Nike is also headquartered there.
Eugene: The only city which could arguably be described as more liberal than Portland. Home to the University of Oregon, it's been a hippie hotspot for over 50 years. Think a more toned-down, laid back Portland. But definitely with the college culture and a slightly different feel.
Willamette Valley: The vast expanse between Portland and Eugene. Salem's here, same with McMinnville, Albany, Corvallis, Lebanon, Woodburn, Newberg, Dallas. Politically it's fairly mixed. Most of the cities lean Dem (some much more than others) but the rural areas all vote Republican. It's the only place in the state where you'll get a feel like it could be in middle America cause of the 100 miles of farmland.
Coast: No major cities but tons of small towns. It's very scenic. If you're into surfing or thinking sunny beach you're not really gonna get that here though. The water's always freezing. Main downside is if an earthquake hits you're screwed.
Southern Oregon: Oregon's version of Appalachia. Rugged and mountainous with a lot of logging industry. Well that mixed with the very hippie Ashland and more than a few weed farms. It's a pretty area. Conservative for the most part.
Central Oregon: Home to Bend and the last Blockbuster in America. Perfect if you like the outdoors. It's right by some of the tallest mountains in the state plus lots of hiking destinations and scenery.
Eastern Oregon: If you wanna be left alone, move here. Bonus points if you're a Republican. Lots of ranches, desert, small towns, and rugged wilderness. There are a lot of unique parts though.
Politically (in case you're BRTD) Portland, Eugene, and the Portland suburbs are solidly Democratic. Willamette Valley, Central Oregon, and the coast are swingy and southern Oregon (outside of Ashland) and eastern Oregon are Republican.
And for the purposes of the poll I'm gonna count Springfield+the surrounding area with Eugene and Columbia County with the coast. I could add more regions but it's never gonna be perfect.
Exactly this and for the reasons stated, with the exception that I would prefer the coast over the Willamette Valley.
Poll
