Thank you all so much for your replies! It gives me so much to think about, most of which I already was, with real examples. I just want him to be happy and he is happy learning! I have a PT conference next Monday so hopefully I'll get a little insight. I've decided that I think I might at least mention a grade skip and see what the response is.
I know that I would have been fine being skipped and my mother regrets not having done it. Unfortunately DS5 is not me. I wish I had a crystal ball right now! lol