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I see that you have him in martial arts, which is great. Does he have friends who will be in sixth grade with him, in the same school, at least? That helps when he sees friendly faces.
Is it possible to visit the school during the school year, when school is in session? I know with private schools, they encourage kids to spend a day in the classroom as part of the admissions process. Since there isn't an "admissions" process here, maybe he can visit a classroom with a friend for a morning? Attend the school field day as a spectator? participate as a home schooler in the district science fair? At least take a tour while school is in session? I got these by saying "we're not sure if we will go to public or private school and we want to compare and see how the kid reacts and what questions he has". Total eye opener for everyone involved.
Middle schools often have an orientation week because it is a transition for all kids. So find out from the principal what is involved with that as well.
Just a few ideas off the top of my head - not being a homeschooler or knowing what is available in your area, I don't have expert knowledge - but something to think about, maybe.
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