Hi montana - welcome. Wow - you've got a lot on your plate right now! i don't have a lot to add, but your latest post made me think of a few things.
One - I liked Miraca Gross "Exceptionally Gifted Children" if you're looking for citations. I think she talks about all the major studies on HG kids. Borrow the most recent version - it has updates on all the kids.
Two - We have been wondering, worrying about acceleration of our DS4. I think this really, really depends on your kid's personality. I was young (late summer bday) but miserable in school, and if I had known skipping was an option, I would have begged for it. I finally got to do dual enrollment in my senior year of high school (taking all my classes at the local university), and I was so glad to finally be free from school! All my good friends were never my agemates. My DH was young (early fall bday) and hated being smaller than the other kids for sports. We would prefer, if possible, to have our kid with agemates but with subject acceleration, at least to start out. But as time goes by, DS keeps on learning, and things change, so we don't know where he'll start school next year. We are happy to have learned here of homeschooling as an option, just in case. Also - all the bad history your family has related to skipping can actually be a positive for your DS - you know what pitfalls to look for and what to explain to him ahead of time.
Three - This board is full of wonderful, supportive people with kids who have tried and done well or not so well in many, many different situations. What doesn't work for some, definitely works for others. And what works for a few months may not work later. Don't be surprised that you'll probably have reassess education every once in awhile. But luckily, you won't have to go back to square one, because I believe with each reassessment, you will have learned at least something about how your child learns.

Good luck!
P.S. - I have a short boy too!