21 days in Oregon suggestions? Is it doable?

Planning a trip with my wife, so TL;DR: we’re seniors, September ’27, dividing by “regions”, going counter-clockwise with a rental car and staying at least 2 nights in each “base” (hotels and b&bs), does it look reasonable?

(Well it will actually be 22 days, but saving the last one next to the airport for piece of mind).

The map is just a basic idea on where to stay as we drive southbound the coast then back north passing by Crate Lake then Bend.

We will be skipping major cities (with Bend being the biggest we’d be staying at), with a more relaxed pace and using home bases to visit the surrounding areas. I understand that will be lots of back-and-forth, specially throughout the coast, but we don’t mind — we rather do that then staying at a different hotel every single night. (My wife “needs” a bedroom with a private bathroom at a hotel/b&b, so motorhome and camping is not an option)

Not sure if we should loop Mt. Hood/Columbia River Gorge staying in Hood River or Government Camp/Mt. Hood Village, any suggestions? (3 nights, with 2 full days and a half to explore)

Any suggestions and inputs are appreciated, thanks.

Author: DudasManolitos