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Small communites that I like are Independence, Silverton (my favorite small community), and Keizer (35,000 or so people). You would not have any trouble finding a home in that price range in those towns.
Other towns that are going through some rejuvination are Stayon (very affordable) and Monmouth.
I grew up in Illinois wearing my "Michelin Man" snowsuit so I hear you. In Oregon you do need a good pair of rainboots and a good hooded raincoat. My kids love puddles...Also we do have several indoor kid parks here in town. Most are located in churches, but a new one just opened up in town called NW Kids Club. It's meant to get out of the house when it is nasty outside.
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