Wolf is now average to below average height for his age. He was in the 95% when he was younger. Height can vary dramatically from year to year. Height didn't even come into our decision about early entrance for him, however he also will probably never be in a "regular" same-age (or even close) class.
The big thing for us was would he be happy. He would have been bored to tears without it and might have become a discipline problem. He is a social butterfly with no trouble making friends or fitting in if he doesn't steamroller the kids with whatever is on his mind at the time. If we couldn't have differentiated his school work to the dramatic point we have then I would have wanted a double skip for him at least. The problem is that we aren't dealing with a regular classroom situation so we aren't dealing with that strict pecking order hierarchy. I'm not totally certain what I would do in that case, one skip for sure, but probably not more, fight to find balance somehow.
Bear, on the other hand, is not good socially and has behavior and developmental issues. Although he is more than bright enough to academically do well with a skip, emotionally and socially he is actually behind. Pretty much no matter what school situation he ends up going into a skip will be really far down our list of considerations.
I wasn't skipped due to the social girl reasons. I would probably have been better off all around with a skip. An acquaintance of mine was skipped and was miserable with it. It's totally up to the individual kid.