No crystal ball but ask yourself whether you are a glass empty or a glass full type of person. This will make a difference. For example, if you are a glass full type of person, you are more likely to notice every instance down the road that affirms the soundness of your initial choice. Regardless, know this: There is generally not one right decision at a particular point but rather a series of adjustments we make along the way, which of course depends on what we have chosen before.
There are so many variables at any given point that you first need to understand your personal priorities and what should be priorities based on your particular child's idiosyncrasies. Because you described your DS as anxious and highly sensitive, I would examine your choices through that particular lens to avoid harm above all else. It's truly a balancing act. For example, while a little boredom never killed anyone, persistent unrelenting boredom year after year can also do real damage.
DS11 just started middle school (6th - 8th grade here) so a lot can still change between now and adulthood. However, I am glad that we chose not to grade skip him when it was on the table in early elementary. We did double subject accelerated him in math (during 2nd and 4th) so that he is studying GT Geometry with 8th graders this year. Interestingly, one of the reasons that we chose not to triple subject accelerate him was my concern that Geometry might be a weak area (based on his relative visual spatial weakness) so that I wanted him to be older when he took the course. At the time (two years ago), our district GT math sequence placed GT Geometry after GT Algebra II so that DS would have turned 12 before studying GT Geometry. However, due to Common Core, our district changed the sequence starting this year so that GT Geometry now comes before GT Algebra II. Ironically, this means that electing to NOT subject accelerate an extra year two years ago still resulted in DS taking GT Geometry at age 11. Who knew? As it turned out, based on a recent geometric reasoning assessment, DS is still an outlier and presumably well beyond ready for a course requiring geometric proofs. Now you can interpret our choice two years ago as a mistake since the district ended up changing their math sequence this year and it turned out that DS was ready for GT Geometry at age 11 so that he could have/should have taken GT Algebra I two years ago and GT Algebra II last year. However, it's actually all good. I don't have regrets partly because DS' GT Pre-algebra teacher two years ago helped lay that strong foundation in Geometry since many units in that course covered Geometric topics. DS would not be as strong in Geometry now if he had taken GT Algebra I instead two years ago. That's not my way of rationalizing or claiming that we made the best choice - only that there can be good found in many choices and it does not necessarily have to be do or die. HTH
