I like it there, but I can't answer your questions since I have never lived there.
Side question for those who have: is the mountain biking there decent? I know there is a trail system there, and I've been meaning to check it out.
Anacortes is in the the same sort of "rain shadow" that Sequim is in. Thus it is often dry or drier there when it is wet everywhere else on the west side of the mountains. That goes for climbing and whatever else...I'm curious if the mtn biking is worth a trip when everything else is getting wet.
As far as the climbing, I've only been there three times. One thing it does have going for it: the views are stunning.