I think I need to go to counseling before having my kids start school! they don't deserve having such a traumatized nutcase advocating for them.
Did seeing your kids have positive experiences help you overcome your own baggage? So far, I've been (mostly) pleasantly surprised by my child's preschool teachers and it has been helpful for me, too. In the preschool's case though I felt an immediate connection with the headteacher who I could tell had an incredibly open mind, a wealth of experience and the readiness to let go of (most, let's not get greedy) pre-conceived notions which has helped me trust that my child might be able to deal with the rest of the staff who does not demonstrate these qualities (in theory, she's his classroom teacher too and he loves her, but she spends more time doing admin in the office than the classroom. I shall try to draw her out on the subject of the elementary principal, after all she should know her really well as they have to work closely together, because I do trust her opinion in most matters).
On the subject of K or 1st grade:
he's a kindergartner now. Formal school starts in 1st grade only, and K is a pull-out program in pre-school. He was entered on the recommendation of the preschool teachers, which is merely informal and is not binding upon elementary schools (in fact, schools are sometimes quite unhappy because parents and children expect it to be and may insist on early entry into 1st even though the school is against). So it's either 1st grade now, young for grade (he's only born about 2 weeks past the cutoff or 1st grade next year, old for grade). I do not think that he (nor the school iykwim) would be good candidates for a grade skip, so this is it as far as acceleration goes.
You aren't a nutcase. It's totally natural to be want save your child your own heartaches. Believe me, I still freak out internally at every transition but I've learned not to "borrow trouble" and let the kids have their own experiences. They haven't ALL been good. We just pulled DS 11 out of a program he loved because of bully issues that just couldn't be controlled (not for lack of trying on every part except the actual bullies and their parents.) We have decided to pull DD 14 out of her current high school end of the year... lovely interest based classmates but she is hungry for intellectual depth and discussion that no teacher or student seems willing or able to give her. However, because the kids experiences overall with school have been so positive and because to date, it's always been clear that the adults around them listen and take action, these issues are only unfortunate... not scarring. My kids still love school. They know they have a voice and that anything can be fixed one way or another.
We have dealt with tools before. DS had a principal that was just an idiot when it came to gifted education. He was condescending and totally ignorant. However, the staff was smarter. The parents were active, involved and vocal. Everyone worked around him and in 2 years, he was quietly removed from the district.
If your DS isn't given early enrollment this year, anyway he could just skip to 2nd next year? Those cut-offs can be frustrating. In our area, he'd make the cut by more than a month.