The Cascade Loop is great! I have personally covered all of that ground multiple times at different times of the year and loved it! My brother lives in Spokane and I used to live in Oak Harbor (west of the loop on Whidbey Island) so I always had an excuse. As far as time, you COULD drive it all in one day, but it would be one hell of a drive. I would give it two to be fair. Three is you stop a lot. In my opinion, Winthrop would be the best place to stay overnight. You'll love the western theme they have going there. Also, I would suggest that you go counter-clockwise on the loop. Hwy 20 is the best part in my opinion...save the best for last! Good luck and see you in Everett!