This is exactly the thing that is in the back of my mind for DS9! We don't want him to miss out on his favorite teacher for 5th grade next year, but if there are grade skips in his future (he skipped K, nothing else), middle school would be a great thing to skip over as much as possible. I'm thinking maybe skip 6th and 7th and start middle school as an 8th grader, but by then he will be in high school math, if not long before that. They are all on the same campus here, so that will help.

Keep in mind that if there are sports or other competitions in your DD's life, she might not be allowed five years of eligibility, so it would pay to keep her on the books as a 7th grader if possible in that case.