Upvote:5
The aircraft is a Howard DGA-18, and the pilot might be Earl Shaw of Dade County, FL based on the FAA registration number history. The FAA stopped issuing "NC" (the C stands for "civil") numbers in 1948, although the earliest registration record in the FAA database is from 1955. The airframe (serial number 602) was manufactured in 1941, so best guess on when the photo was taken would be sometime in the 40's or 50's.