Puffin and Howdy, thanks for telling me your experiences. My instinct as well is to let him play, since he's settled in school, happy, and as a proper little boy, loves playing.

He already feels like a little man since he's matured so much over the last year, but I couldn't imagine him in a class with desks and writing exercises.

He scored very highly this year on a maturity assessment, which is dramatically different from last year when he had a number of meetings about emotional control, so DH thinks he may be more ready to handle a skip. Perhaps it's also a good sign that he's already caught up to his peers socially/emotionally and will be mature enough for later skip if it's warrented.