Welcome to OR!! I moved here from PA a few years ago. The cost of living is higher in some areas (near cities) but most are very reasonable. It does tend to rain a lot through the winter so everything stays very green. It's really pretty compared to a lot of places. The ocean is cold as #$%* all year long though. Pack your waterproof wool knickers.
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Unless it's biting cold, icy or snow covered, which doesn't happen that often, I ride all year long. It is drop dead gorgeous out here. Riding through the temperate rain forest on the way to the coast with the cedars surrounding you and the moss hanging, everything brilliant green all year 'round... WOW.
FYI: You'll be close to the WA state line so when buying something over there, show them your OR license and they should not charge the sales tax.
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Bend is very nice. It's the high desert so it stays cooler in summer and warmer in winter than many places out here. It is rather dry though. If dry works for ya, great. I have a hard time visiting for more than a few days because my skin and lungs are too sensitive to the dry air.
I looked it up... the income tax is 9% here if you make over $7600. I would rather live and work in WA. They don't have income tax but they do have sales tax at 6%. I'd rather pay 6% of a tiny bit of my income than 9% on all of it.