It sounds like he'd be fine acadmemically in kindergarten. I wouldn't be so worried that the school admin will be out to get him, since from her perspective he nearly meets the cutoff, but there's simply a possibility that he won't behave properly since he's on the young side; she's being reasonable by offering the trial period. I would do my best to prepare him to fit into the classroom routine. Impress upon him that he must behave or he'll be out, and back to boring preschool. Find opportunities for him to be in classroom settings before then, if possible, perhaps with local classes of some sort.
Good points.
We told Mr W pretty much the same thing and he knows he is under the microscope at his new school.
Something else to consider is that its still 8 months away so you have lots of time.
The biggest thing is to work on independence stuff. I would visit the K class and observe to see what will be expected of him. I'd also talk to the teacher to get her take on what she expects and what some problem areas might be.
