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So I have a July Birthday and was one of the youngest in my class and really not mature enough to start kindergarten. My parents held me back and I repeated K. It was probably the best thing they could have done for me and going forward I was generally ahead academically and had a better maturity level.

So when we were planning on when to TTC we knew that we would plan around the cutoff dates. In NYC it is a very rigid 12/31 and they do not allow redshirting. We were very lucky and DS was born mid January. Currently due with #2 in March. I want to give him whatever advantage I can given what I know it did for me.

Probably not, but I don't know. My son's only 4 months now but if we stay where we are and stick to the rules he'll make the cut off by 2 weeks (and be youngest in the class), but if we move he'll miss the cut off by 6 weeks. So either youngest or oldest in the class.

If he's doing well I'd prefer to just send him when he's due. But if there's a really high rate of redshirting, I may have to reconsider. I just wish everyone stuck to the rules.

DS1 was born August 31 at 11:14PM so he is right there on the cut off. My MIL already suggested that it would be good to hold him back because he will likely be little but we'll wait and see how he is doing with learning and maturity before making that decision. He is only 16 months now so it is too soon to know.
I was one of the youngest in my class growing up and my second grade teacher wanted to hold back not just me but the other ones near the cut saying we were immature. 2 others got held back but I did not and I really did not struggle with school academically or socially.
I don't understand the Sept 1 cut off - why Sept 1. It used to be October here and I know some places it's December.

@Orchid: We do this too. Although I'd say that while we do smaller amounts of "school" than traditional Kindergarten occupies in terms of time, it's not lighter as a substantive matter at all.

I read on aha parenting that holding a child back a grade (due to failure) can have long lasting self esteem impact. My brother was held back between 2nd and 3rd and he had massive self esteem issues related to it after puberty hit. As a result I am not keen on redshirting but I would consider doing a private half day kinder as a compromise.

ETA: I have a 3 YO born in August.

DS1 is a 9/6 birthday and if we went to public he would get pushed back a year. That itself would be fine but DS2 is due in mid May and they would be 20 months apart. I don't really feel like making them one year apart in school because of a 5 day difference from the cut off. People around me have told me to red shirt DS2 to keep them two years apart and that sounds even stranger to me. Obviously it would depend on readiness more for me but barring some problem we are going to send our kiddos to a local private school that has assured me they base kinder entrance on readiness.