Hi Luke:

Well, since you are a Real Estate Pro I expect you'll understand this when I make the disclaimer, 'This is not steering.' But I've recently visited Astoria and Florence. I enjoyed both tremendously. There are lots of great places in between. Good luck with your search.

My wife and I are also considering the coast as a part time place to live. We have driven the entire coast and then returned to stay in places we lived to get a better "feel" for the town and the people. Rather than give you specific town to consider, I'll just pass along our thoughts: Most of the places are very "small town" (which we like - coming from phoenix). The Northern part of the state is more "touristy," but still very pretty. The southern part is our favorite due to the following: The redwood forest is close and in some cases nearly down to the water's edge. Post card views of cliffs with crashing waves are more frequent that not. The further south you go, the less rain (in general). The people tend to be friendly, but reserved. These are not party towns and the majority of the residents want to keep it that way (we also liked that.) Be aware that the weather in the winter is very dreary and do not appeal to everyone. The only way you will know if Oregon is in your future is to start at at one end and spend a week or two driving. Good luck.