My son has an early June birthday - he started in the fall. Thankfully he didn't mind "easy" work, and had always been happy to go with the flow - but if he had been held back a year, it would have driven even him crazy. We chose not to skip - partly because of his age, but also because he was (and still is) the smallest kid in his grade. The school were great - accelerated him a year in math from 1st grade and up. He is now 11, in 6th grade, Middle School, on the Honor roll in the full time gifted program. I just cannot imagine him still being in 5th grade at this stage. If you held him back, could yu put him straight into 1st grade the following year, if you thought he was ready ?