We're in Portland! But I office out of Seattle and have to come up once a month or so. When I do, we typically make a weekend out of it.
I'm yet to pull an Enchantments permit. But we have a lot of foot time around Snow Lake; and I have even more ski skin time all around Alpental valley! We also love, love, love Lake 22 in Baker Nat and Colchuck when the larches are firing.
You are right about the vastness of this corner of the world. We've done so much, but so much left to do and so much we want to do again. I do make it to your neck of the woods every year, without fail, to ride SR20 before it opens to cars and Port A > Hurricane Ridge > Obstruction Point the first Sunday in August (annually closed to cars and bike only that day). It's so dumb, but seriously, it's peak Earth. There's nothing better for me. I just need more time to sneak up on Baker to ski. Hence, I'm picking up a Sprinter next week

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All OR beaches are public which is very cool. Wife loves the Gorge as her main hobbies are waterfall hikes and wine. Hood River is very dope (Post Canyon if you're into MTB; river front is great for kids + Pfriem / Ferment have to-go windows, I.e. kids play / water play while you sip a beer!). Across the river, Gifford has a lot to offer and Adam's is probably the most remote I've been in WA. Again, I love Bend. It's similar access to what you have. Bach is 20 min. Cascade Lakes Highway. Great backcountry skiing access on any of the Sisters, Broken Top, Jefferson Wilderness. Phil's MTB is connected into the town. Awesome beer, the town is clean and modern, Deschutes is beautiful, Smith Rock, Sisters, Tumalo Falls. And everything, in all directions, is Deschutes Nat - your land, enjoy all of it and disperse camp baby! And you can go from high desert to PNW dank in 45 minutes up the Santiam to Willamette Nat, which is just wild!