You are asking great questions, Hils!
These are frequent topics of conversation, many here have BTDT.
I'm not sure what testing would be expected by the school district to grade skip
This may vary immensely... from nothing, to being required to make a
pre-determined cut-score on end-of-year grade-level tests, to a complete
IAS process... or anything in-between.
I'm on board with letting him make the decision...
To assist him in making an informed decision which he can "own," you may want to have discussions with him about issues raised in the acceleration roundup (linked upthread)... such as not being able to drive when classmates are, etc... to afford him the opportunity to consider
future implications.
maybe even see if the Jr. High could let him take a day to see what high school is like
Yes, a school visit and a day to shadow are great ideas, to help assess "fit."
Lots of conversation about the best possible efforts to meet each sibling's
needs may be helpful.
Along those lines...
lists of common strategies to help 2E, in case any of these ideas may be helpful for your eldest son, but not yet being implemented.
These posts about having an older sibling in the receiving grade, may be of interest:
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post 1 (March 2014),
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post 2 (Oct 2018),
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post 3 (Oct 2018).
