I have zero clue what any of these things are. I know I could start googling around for them, but would anyone here be willing to pitch one of them to me and suggest a good starting point? Seems like people are really excited, and I rarely have my finger so far off the pulse.
When They Cry is kinda of an anthology series written by a japanese doujin (indie) novel creator named Ryukishi07. It started with Higurashi no Naku Koro ni (Higurashi: When They Cry), a mystery novel about several murders ocurring in a small japanese village. The story is centered around the various bizarre events that happen in that village and let the reader try to figure out what's happening. It's hard to say much without spoiling, but it was very well received to the point that it became popular enough to get an anime show, several manga adaptations and various console ports with added content and improved art. Higurashi is divided into two parts (When They Cry 1 and When They Cry 2), consisting of four separate novels for each part for the original releases.
After that he wrote Umineko no Naku Koro ni (Umineko When They Cry/When The Seagulls Cry), a new novel unrelated to Higurashi, but similar in structure and some themes. It's another murder mystery story, but this time on a "smaller scale". It's about a rich family going all to a small private island, said to be cursed by a witch, and getting stuck there due to a storm. Murders start happening and the story is all about trying to understand what's happening there, who's behind the murders or if that's just the witch's doing. It's also divided in two parts (When They Cry 3 and When They Cry 4). It's very inspired by Agatha Christie's
And Then There Were None.
It's hard to go in depth about what makes these stories unique and interesting without spoiling the most important aspects that elevate them. The games themselves are just basically visual novels without gameplay at all.
The new announcements in the OP are When They Cry 5, a brand new story named Ciconia no Naku Koro ni, that will likely have some shared themes and structure with the two previous stories (Higurashi and Umineko); and a brand new novel for Umineko -- I actually don't know how this is going to be as the story was finished already, but we'll see.