Movement/Transportation: Most people in Oak Harbor drive a car to get around, or walk if they are close enough to where they need to go. Island Transit provides public transportation in Oak Harbor and the surroundings. Bus fare is free.
Island Transit -
Newspaper: The Whidbey News-Times is the local paper in Oak Harbor.
Whidbey News Times - Local News, Sports, Entertainment
Technology: I don't quite understand what you mean by this question... Oak Harbor has high-speed Internet and cable TV if that's what you are wondering.
Climate: It has sunny and warm summers, cloudy wet and mild winters, and spring and autumn are in between. It's in a rain shadow and gets less rain than its surroundings. There's usually one or two minor snowfalls in the winter.
Clothes: It's a military town so when not in uniform people dress pretty casually (T-shirts and jeans).
Farming: Oak Harbor is in a fertile region. Hay, alfalfa and wheat are big crops in the area. There are also some small ranches. There's a big fruit/vegetable farm north of Oak Harbor.
Entertainment: It's not a huge city so options are a bit limited. There's movie theaters (I think there is still a drive-in outside of town), restaurants, parks, and a bowling alley. There's boating in the harbor, and outside of the city there's hiking, camping, and fishing.
Radio: There's quite a few radio stations in Oak Harbor. Here's a list of stations supposedly receivable in Oak Harbor:
Radio Stations in Oak Harbor WA (no idea how accurate this is)