Yes I rode the Chilly Hilly - I live in Kitsap county and my local rides are on very similar terrain.
I fully plan on enjoying the scenery - quite a contrast to the green side here. I like the challenge of the hills and am leaning toward #2. If I hit my limit I can always just turn the bike around and head downhill and call it a day.
I will be returning on Saturday after the ride but I like your suggestion.