Our DS skipped 4th this year midyear and it's gone well. He's still closer working on building friendships (he's pretty introverted), but he loves his class and his teacher, and he found a couple kids who seem to keep him challenged. I think what really worked for him in moving ahead was being more autonomous and in depth with projects -- the higher expectations of personal responsibility in class were really appreciated. He can take things to the next level. He's chomping at the bit for more, which makes middle school look appealing in the fall, but he did express dismay that the 6th graders don't have recess, which is a pitfall of losing a year of a younger grade. But they will at least have P.E. every other day. There's really a lot to weigh, and I'm not sure yet if DD will also do a grade skip or not. It's such an individual thing, as the others have said. DS was an easier decision, I think.