I spent a year in Coupeville on Whidbey Island, and I would recommend it. It is part of the rain shadow, so gets around half the amount of rain as seattle. The summers are surprisingly dry, with lots of fog coming off the sound and gorgeous afternoons, and the winters are cooler and more damp with regular drizzles. You might see one thunderstorm during the summer, but they are not often. Prevailing winds are common, but lots of room for micro-climates with rolling hills. The more south you go on the island towards Langley, the more wet and overcast it becomes- only part of Whidbey is technically under the rain shadow. You're constantly reminded of water's presence while also being grounded by Mt. Rainier, Mt. Baker, and the Olympic mountains on the horizon depending on which direction you look. Also, the people are great- tons of local producers, homesteaders, farmers (organic), artisans, musicians, etc. Couldn't talk it up more
Happy plans to you!