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The answer depends on what other climate limitations you might have. As a broad general rule, the closer you get to the coast, the less sunshine and warmth you can expect. Southern Oregon is generally sunnier than northern Oregon. The southeast, near the Nevada border, has the sunniest weather and the warmest summers. The sunniest areas in Oregon are also the coldest in winter. Proximity to the ocean increases temperature mildness, but also increases cloud cover.
A lot of people are looking for a mix of good summer weather and mild winter weather. If you don't want winter snow, then you would be limited to areas west of the Cascades (which are not as sunny as areas to the east). The Willamette Valley is populous for a good reason --dry sunny summers with long springs and falls. Winter is four months of rain.
If you go to the Western Regional Climate Center's website and click on "General Climate Information", you can get national maps that show hours of sunshine and degree of sky cover.
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Where's the best (warm/sunny) weather in Oregon?
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