1. You should have a lead for the Organisation (in the envelope icon on the top-right of the screen). If not, then you might not have met up with Gramps in the mountains and done his pigeon questline (you open up the mountains by checking the note in the Manor's garden)
2. Each girl can only give birth to one child. If you want her to get pregnant again after that then the previous child needs to be sent to Artifact (only one child per girl can be in the day care at any time, and the girl can't get pregnant is she has a kid in the day care)
Hope that helps! :)