Kindergarten or not? to hold back or not that is the question..

I am a preschool (ECE teacher) for almost 20 years, and my experiences tell me that it is difficult to make a decision as a parent what we want the best for our child.  Cory is at this level where we realized that he is not ready for "mainstream" approach at our local school.  He is approaching age-appropriate all area of developments except for speech.  We don't want just put him in Kindergarten at Carrie-Anne's school and then do "wait and see"...I am afraid that might be setting him up for fail.  I did thought about him going for another year of preschool but I know too well how school's protocol works.
Ideally, anyone who withheld their child from going to Kindergarten, (for another year of preschool,) the school district will AUTOMATICALLY put them straight to grade one without a question! then you're stuck with negotiations, and trying to push for going to K instead etc will be a long battle.  Its just that they are pretty firm with age - year following levels.  From my experience, it's BETTER for Cory (or any other kids) to go ahead to Kindergarten whether they are not "ready" or not.  The school can START their own evaluations or assessments during that time, and if there is any concerns they can work on it during that time.  Rather than delay when the child is in grade one..you would have to wait another year...which its not good in my experience to delay any further.  The early intervention, the better, so therefore don't want delay Cory's needs by holding him back.  The school has a different procedures, policies, its a whole new ballpark and they prefer to do their own thing.  When it's a better time to do it? Kindergarten or grade one..it's not hard to figure that out.   If then, Cory needs to repeat Kindergarten, fine by with me.  Its better that way.   I know I want him to attend another year of preschool, because it's feeling safe and not wanting to let go in that scary new world out there and I want him to catch up.
But I do have to let him go and let the nature take course with the school district. the sooner the better.  They can work with him and if needed, they will help and get the resources we need.  It's better now, not wait until grade 1.  I am also afraid if I held him back, then in following year, they will put him straight to grade 1, not Kindergarten!  That happened to many kids, I heard.  Some districts are strict with that.  Don't want to take that chance.  
Look like we need to find a resource type of school for him so he can get the resources he needs to work on, rather than our local area school.   In few years, maybe he will be ready to attend Carrie-Anne's school some day.   It is our jobs to help and work with Cory for few more years.