Hi Allison,
DHs can have great insight into the social scene for boys. I learned from my DH that there is a pecking order, and size and skills do matter. ((Think Napoleon Dynamite: "Girls like boys with Skills.))
I'm guessing that you come from a part of the country where sports competitions matter, and when that happens you will get plenty of red-shirting for sports, in other words - if he's little compared to his age peers, you are kind of off the hook asking for skips, because he's going to have his size as a strike against him even if you hold him back.
Individual sports, age grouped sports, and marital arts are all ways to give boys status and moxie, which will never fully the place of size, but will certianly help. We live in a totally unfair society, that judges men on size, particularly in the early years (Later income eclipses size, yes?) But a child who is at peace with themselves, has the love of his parents, has reasonable social skills, and some academic skills, and maybe a great imagination, or enclyclopedic knowledge of boy-esoterica, can find a way to find a comfortable place in the pecking order.
In a way, a small grade-skipped kid is better off that a small ungradeskipped kid. I don't really think that the size stigma is dose-dependent, and older boys find a brainy shrimp who pays them homage more palatable than a hulking grade-skipped brainiac who challenges their status. A small unskipped kid is just small, unless he's fast, or especially good at something. Dottie's kid is third born and knows how to not rock the boat of older, higher status kids, but my tall, loud, only child wants to lead, thinks that all should agree. He does better socially with boys who are 2-3 years older and more self-confident than he does with boys who are 1-1.5 years older, and less secure.
Ask you DH lots and lots about his own experiences as a small, medium and large boy. I have found a whole, previously uninteresting world of status while looking through my DS's eyes. It reminds me a bit of the joke about how the President must be popular with many many people, while the Vice-President must only be popular with one (the President.) As far as social rank went, I only was concerned with the few friends of my heart, or the current boyfriend, while my DH grew up trying to please everyone.
For me growing up, being overly concerned with status was a luxury that I just couldn't afford.
I hope this helps. My hunch is that your son has already shown that he is quite sensitive to being educationally malnourished.
Love and More Love,
Trinity
