Wildcat, I think YOU would like it. The best way to evaluate the rain issue is to look at the stats. Take our rain stories cum grosos saltos. However, consider the culture of Gov Tom McCall who proposed that visitors should be required to post bond that was returned upon departure.
There is an attitude in the NW that new arrivals are to be discouraged.
Portland is a 'dine out town', it is also a community of readers. My daughter used to go on dates to Powell’s bookstore. Housing isn't cheap, however. The area has experienced significant population growth.
My bias is great public schools and at least the availability of cultural activities.
In addition to Ashland, Hood River is worthy of consideration. Hood River is known for wind sailing, not cultural activities. Google is moving to The Dalles, just east of Hood River. Generally speaking the arrival of high tech improves the public schools.
Bend is also very popular and has grown like crazy. Consider Sisters or Redmond. Cold in the winter, hot in the summer, very little rain.
The NW is dissected by the Cascade mountain range. The mtns wring out moisture as the weather systems head east. East of the mtns is a high plateau that is relatively arid. The Columbia River Gorge is a wind tunnel.
A little known part of Oregon is known as the Blue Mountains, near La Grand. Take a ride down the Snake River between Oregon and Idaho at least once in your life.
Then there is Gold Beach and Brookings ...