Thank you for all of your replies and advice. I would love to hear more if anyone else would like to chime in with additional thoughts. My son has certainly not considered the social ramifications, at least not yet, but would probably be fine and perhaps we are overly cautious as he is our oldest. We are still waiting on some of our supervision questions, but are generally inclined to let him go. The one remaining concern is that other parents (of older children) told me that this is the grade that the girlfriend/boyfriend thing starts. Not thrilled about that even if he was 11 or 12 (I think 6th grade is way too early), and he clearly is not interested in this yet, but I don't want him to be uncomfortable when that topic is discussed by his peers.
To answer frosty's question, grade skipping policies seem to be all over the map. All of my children have grade skipped at an early age except for my above mentioned son (mostly by only 1 year at this point). My kids attended a very progressive preschool/K that helped tremendously when they saw our 3 year olds reading. My fourth grader is our oldest, and quite frankly, we didn't know better when he was younger to skip him earlier.
A great help is the book "A Nation Deceived" which you can download as a PDF. We gave a copy to my son's school and they actually took the time to read it. I think that grade skipping is easiest at an early age. Your 14 year old must be in high school, can't he just take upper level/grade courses? The modular nature of most high school schedules should make that easy.
