Tough decision given that the 2nd grade teacher is cooperative. A couple of things that jumped out to me was that 1) He would have to go through the 3rd grade teachers anyway but next year when it would be even more boring for him. This year the work would be more challenging so less accommodation would be required. 2) I think it is better to skip earlier, especially if another skip might be necessary. My DD10 just skipped 5th and now I am just understanding how little she was actually learning in school at the younger ages. It seems to me a younger skip is an easier adjustment socially and academically, but I don't know what experts say.