I feel like reading or reading about Ryukishi07's interviews and blogposts really enhances the context and understanding of his works, including When They Cry of course. It's really revealing how his personal life, including his poverty and background as a social worker, and how they and history inform his political beliefs really makes things click as to how When They Cry came about and why it is the way that it is. I'd also highly encourage paying attention to the japanese historical and social context involved and to seriously read up on it. Higurashi, Umineko, Higanbana, Rose Guns Days, and Ciconia are all heavily informed by these things and you will enjoy them all more by paying attention to these aspects.
I need to play Rose Guns Days for Meryl Tanashi. I just know that whenever Ryukishi writes a blonde girl it’s inevitable for me to obsess over her. It’s like they’re all made to cater to my tastes. You can even say that since it’s no longer a possibility it’s certain to happe- *shot* okay all the lame jokes aside, I wonder if the manga is any good. If it’s not I’ll just buy the VN and install Witch Hunt’s English patch
If you're wondering why some seemingly more obvious choices are missing, I only picked characters with next to no redeeming qualities in their respective novels. Literally there to be sacks of dogshit from start to finish with personalities pushing how fucked up and evil they are.