DD2 was born the end of August. She makes the kindergarten cutoff by one day but they start school mid August so she will be 4 for the first 2 weeks of kindergarten. DD1 was born mid May and is currently the third youngest kid in her class so DD2 will most likely be the youngest by far. Her birthday parties are going to be a problem. Right now, they are around Labor Day, no one is ever home. After school starts, she will be too early in the school year to have any school friends at her parties. This summer, we went to the beach and she was too small to ride the rides she wanted to ride but big enough to know she wanted to ride them. She was too young for swimming lessons and summer camps this year but will be one of the oldest kids in the 3 year old group next year. Being pregnant over the summer wasn't that huge of a deal. Really, it was one summer. I probably wouldn't wait if I were you. You don't want to risk having a baby closer to Thanksgiving/Christmas/cold and flu season. And while I love having a kiddo with a May birthday, it looks like you don't want to wait that long. Good luck!