The Packard is a 1949-1950 and is in pretty nice shape. With the best resolution I can get, the flag looks like a 48-star, which would be pre-1959. The parking meters are of a newer design, probably early 1950's. The Federal Building still has 12-light single-pane sash that looks like it needs painted. The recruiting posters appear to be Korean War era. I would be inclined to guess1952 for the year of the photo.