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Also do Wincest! & Quality last just for that 100% conclusion feeling.
In my experience, I needed to "verify game cache" between almomt every achievement.
I recieved the "Move along, pervert..." achievement just my pressing the "Prt Scr" key while the picture was in front.
The picture for the One day Achievement won't be there until the second time you are in the office. You correctly mentioned the level is "whitepawn." I mention this because one player didn't see the picture and this might be the reason.