I can't say yet when the time skip will be done. I can't even say when I'll start with it, as there is still a lot I need to do in the "current" time. I don't expect to start with the time skip this year.
My current vision for the timeskip is a worldmap, where you have icons of various events that take place during that time, and you can interact with the icons to play the events which you want to see. The timeskip will be split into multiple phases, in which these icons will change as the time is advanced by an undefined amount every phase. Women learning about or informing Ryen about their pregnancy, pregnancy itself, birth, and children grown up to some degree are planned to be some of the content which is displayed in these time skip events (there will obviously be other events as well unrelated to pregnancy). However, I can't say beforehand how many characters or which characters will get what kind of events, as the huge amount of children means that it's very unlikely that every child/parent will get the same amount of content.