MADiSON

Not a native english speaker so sorry if something is not correct.
The achievement explains it itself. I counted 27 photos and the achievement popped so here are some tips.

Attic puzzle: You could make just one picture and figure out where the remaining portraits belong to or make two pictures to save time and less fiddling.
Cathedral: Read the descriptions to find out which color belongs to the portraits but I think (not 100% proven) it's always the same.
Jesus = red, Angels = green, The "Man" = yellow, Maria = blue
Take some time and check to which time the candles belong to avoid time traveling like a bunnyhopper.
Section with statues / Crowbar pickup: Listen closely. You can hear grandma whining behind the right statue you have to shoot.
Blue Knees / Grammophons: This is up to you. You could avoid to blend him and getting caught to keep the picture count low or if you play on normal you blend him 2 times up to 3 to ensure you have a more stress free time to play the grammophons.

Something to consider, Idk if this achievement is a little buggy. I needed two attempts to unlock it. On 1st attempt when I began the Grammophones section I had 32 pictures taken and stopped counting because I rushed it but achievement didn't popped. That's why I trimmed down the picture counter even more on my 2nd attempt just to be safe.