Welcome Tigerle. I completely understand how complex your situation is. If only there was a magically easy way to see the "right path" forward. We are in the position of having been offered a second grade skip to our DD 13 and have some of the same concerns re the balance of academics and emotional/social concerns.
First of all I actually saw lots of positive elements in your post.
You have a wonderful son with amazing ability. Despite his challenges he isn't ASD. He has been able to navigate the rigours of the school environment and find friends and join in. He got a great report card. The comments about executive functioning are not unexpected and they will improve. Lots of helpful sources out there. Try Smart but Scattered but remember he is a highly gifted 7 year old. What is going on in his head has to be way more interesting than where he put his socks! And of course the extension work is more to his taste. There is a clue for you.
It is always intriguing to watch how much more organised and engaged my DD is when the "work" is actually interesting to her. Still, don't expect organizational miracles. We have worked hard on those but having a more appropriately challenging school setting helped her learn those necessary skills. We have seen an amazing growth in that area in the last year.
As to all your choices, it is good you have some idea of what is available to you. Short of cloning our kids and running randomized trials, we will never know if the option we didn't choose was the better one. Best to stay flexible. Choices are rarely set in stone although, of course, undoing a change or making a new one is traumatic.
In situations where there is appropriate support, acceleration works well. Note that having the right support is essential as you have experienced. I am sorry you had a difficult time in elementary school. No wonder you have an additional layer of concern and anxiety about making a good choice for your son. It is also important to look closely at the individual and address their needs as well as their gifts. When considering an option keep that firmly in mind as you evaluate different programs, do they see my whole child not just the gifted bits.
Be wary of any setting that places undue expectations on your child. Whatever grade they are in, they need to be "normal" for that grade in the expectations of their performance. They shouldn't be expected to succeed in every way, every day but allowed to struggle and even fail. We have heard a few disturbing comments in our exploration of different educational settings that place a tremendous burden of expectation on accelerated individuals which don't meet our desire to have a child who is appropriately challenged and learning not cruising.
It is so hard. I know. I now need to apply some of what I have written to us as we are considering all educational options this week. Sending you the best of luck. You know the people here get "it" which really is a big help.
