I think Dottie's son skipped several grades at once--right, Dottie? Maybe she can tell you her feelings.

For me, I wish we had skipped more at once so we wouldn't have to agonize over it now. Especially if they're in elementary school and have mastered those topics, I'd rather them get into
"meatier" work earlier. At the time however, my kids dictated single grade only. Now I think my oldest regrets not doing more because it seems harder to skip HS credit/prerequisite structure...at least here. If you son's willing--definitely give it some thought!