Well we know one of the photos was around christmas time @0:40 in the video and know that in franks house in hawaii— if only had the year
I believe the year is 1960. Those two Jazz albums help date it. One is Nat King Cole, (1957) and the other is "Cuban Fire". There were two versions of Cuban Fire released, one was in 1958 (I believe) and the other was in 1960. (Songs were added to the original set.)
I favor 1960 because Stanley Ann was not in Hawaii prior to 1960, and she didn't come back to Hawaii until 1962. Christmas of 1960 works, and it represents the approximate time she became pregnant. (November to December of 1960)
If it IS 1960, and she has a boyfriend, (Barack Obama) What's she doing posing nude for Frank? I don't think it's 1962 because she shows no apparent signs of having had a child. Just my take.