This is from my recent short visit to Portland. I came in late afternoon, stayed there one night and then headed back to Seattle. According to every local that I had a chance to interact on my short photo walk it is very unusual to have clear day in the middle of the winter. So a lot of them enjoyed nice weather and I guess I was lucky too. Clouds were slowly coming in and the following morning we had full overcast with rain.
Portland downtown is not as big as other nearby large cities, it has only a few tall buildings, and they are spread around the downtown area, so it does not have the same “big city” photo ops as Seattle or New York city, but it is very easy to get around it with free tram system and abundance of great restaurants to eat at.