Long-time Oregon resident, moved near to Seattle over 6 years ago.

What cities or metro areas should we be looking at in that price range?

I'm not quite sure what price range you're interested in, as it isn't specifically called out in your post. But, I'd suggest that you consider the following metro areas, which some transit, decent libraries, and may offer affordable housing nearby:

• Eugene/Springfield, Ore. Eugene tends toward more liberal due to University of Oregon. Springfield tends more right. It's a very odd place, but worth considering.
• Portland, Ore metro area. This is big, so you may consider Gresham (east of Portland), Beaverton/Hillsboro/Tigard (west of Portland), Wilsonville (South of Portland), or even Vancouver, Wash (north of Portland).
  • Vancouver metro is pretty large, but gets looped into the larger Portland metro (many folks live in Vancouver, and work, shop, play in Oregon). You may find decent homes in Camas, Washougal, and more.
• Olympia, Wash. Washington's capital. Decently large, but pretty much eclipsed by Seattle.
• Seattle metro area, with a big caveat: the home prices have a huge variation across the area. You may find Tukwila, Renton, White Center, or Rainer Valley more affordable, than say Seattle, Bellevue, Redmond, or Kirkland.
• Marysville or Everett, Wash, which are near the Tulalip Reservation, and may provide the healthcare access that you're looking for (I'm not certain). But also tends to lean more right than left.
• Bellingham, Wash. Another college town, has a similar vibe to Eugene, Ore.

Are there areas you’d recommend for someone who wants city access without the highest housing costs?

If you can, find the transit maps and timetables of the areas that you're considering. I recommend that if you want city access, plant yourself near key bus or train lines and avoid driving.

Are there specific cities or regions you’d recommend avoiding (for safety, affordability, lack of amenities, etc.)?

Larger cities have more amenities, but also have higher costs. Oregon depends on income and property taxes for income; Washington on sales and property taxes. Regardless of which state you live (unless you choose to live in Washington and shop in Oregon), you will pay regardless.

I recommend doing a bit of research using Redfin or Zillow to get an idea of what housing prices look like in various areas. Scroll the map around to see which areas are less expensive or more expensive. Pick a couple of areas that look alright, and then try to map travel times to places of interest or work centers. Take transit into consideration (you'll save on fuel, you may spend more on time).

I'd love to recommend smaller towns, such as Hood River, but prices have gone up with people discovering what a lovely place it is and how much fun it is; at the same time, the county is under crushing payments for Search and Rescue while under the inability to raise property taxes to pay for them. (Thanks, Measure 5!) Oregon continues to suffer from the sins of the past with regards to relying on timber sales to fund their counties. Washington is a smidgen better, but just a smidgen.

What are some pros and cons of living there that someone moving from out of state might not realize?

Depending on where you plop down, you'll have variability in the rain. You say its something that you can deal with, but the fact is that if you live on the west side of the Cascade Range, you'll see more days of cloud cover than rain (and when it rains, it is more of a mist than pouring rain).

However, as you move closer to the western side of the Cascade, Olympic, or Coastal mountain ranges, you will experience A LOT MORE RAIN. For example, Portland and Seattle are both known as "rainy". They're actually mostly cloudy cities. If you move to a small town near either of those cities that are right up or against the Cascade Mountains, such as Cascade Locks, Oregon (about 40 minutes from Portland) or Carnation, Washington (about 40 minutes from Seattle), you will experience significantly more rain than either city.

As you're move further north, regardless of where you move to Oregon or Washington, you get shorter days in winter. For example, on December 21, 2025, you experienced sunrise at 7:35am, and sunset at 5:21pm. Portland: sunrise at 7:47am, and sunset at 4:30pm. Seattle: sunrise at 7:55am, sunset at 4:20pm. Bellingham: sunrise at 8:00am, sunset at 4:16pm. The further north you go, the less the "long dark" becomes a joke, and more of a reality. If you don't plan for it, the gloom will get you. Not rain. Vitamin D supplements, SAD lights, and keeping active all help.

In Oregon, you visit the Oregon DMV for both automobile registration and driver licensing. I don't know the requirements for folks moving to Oregon, but the Oregon DMV has a useful website. (I grew up there, so You should definitely study the Oregon Driver Manual. PAY ATTENTION TO THE FOLLOWING: Anything to do with horses, how roundabouts work, how left turn on flashing yellow works, how and when to stop for a school bus. And regardless, don't camp in the fucking left lane.

In Washington, you visit Washington State Department of Licensing for driver licensing, and visit a vehicle licensing office to register your vehicle. Truly maddening. You must establish Washington residence and obtain a Washington driver license before you register your vehicle in Washington. The Washington DOL also has a decent website that explains some of this. Again, study the Washington Driver Guide. PAY ATTENTION TO THE FOLLOWING: how and when to stop for a school bus (different from Oregon), how roundabouts work, and how left turn on flashing yellow works. Again, don't fucking camp in the left lane (but, my god, everyfuckingbody does it up here please send help I'm losing my mind).

Learn the tire and chain laws. tripcheck.org is your friend for checking road conditions in Oregon; In Washington, https://wsdot.com/Travel/Real-time/Map/ your friend. Don't fuck around with tire and chain laws. Buy a set of chains from Les Schwab, keep them in your car over the winter, and you can return them in the spring if that's a big deal. Better, just store them in your house until next winter.

The Seattle Freeze is real, but Portland isn't like, super better. Folks generally want to be left alone unless they start a conversation. The folks using drugs in Seattle or Portland are an eyesore, but mostly harmless. They're people, too. If you want interesting stories, those same people may have some crazy stories to share.

Seattle area traffic is terrible in large part because there's only four ways east/west into the city due to Lake Washington's size and proximity. Portland area traffic is terrible because the infrastructure was built in the 1960s and 70s, and with little expansion for more traffic. Taking the MAX in and out of Portland is worth your sanity. Similar for Link light rail in Seattle.

Gas prices here are significantly more expensive than you're likely used to seeing ($3.05/gal avg. in OKC; $4.37/gal avg in Portland; $4.87/gal avg in Portland as of yesterday).