What does your gut tell you? I don't know if you remember me and my ds's situation but all last year I was very reluctant to grade skip. I second guessed everything and when it came down to making a decision we leaped. Sometimes my thoughts go to "what if?" or "how do we handle that? or "what if it isn't enough?" but for the most part a giant sense of relief was felt by all
once we made a decision and had a plan. I am not sure what next year will bring but I do feel it is a step in the right direction.
Good Luck.