Did you have sex with both three times? Then you of course also need to be at home with both at the same time.
I think the game counted the child she already had with her ex - husband that she told the mc about.
Pretty sure it does. Shows the same for me with a pregnant Shiori.
The skill books that can be bought from the book store rotate daily. That means if you go check the book store daily, eventually the skill book for shibari will pop out.
I am not sure but I think they do not rotate (i. e. will come again in a certain order) but are chosen at random, so with RNG being cruel it can take a while. In the end your conclusion is right however (word of warning: haven't played 22-2, sometimes stuff gets messed up).
You need reduce her purity with Romance Novel's until she accept new date.
Kylie also needs to assault the MC at night. I mean, you can't send someone to jail just because she stands outside their house for hours at a time every night. There needs to be an actual crime, in this case, Kylie attacks the MC with a taser, tries to rape him and threatens his housemates.
The game just ended for me once I got one of the roommates pregnant, I got the ending and went back to menu.
