My son is 2E. (Gifted +LD), so we did a ton of research and visits before choosing a school. We did open houses starting in 7th grade. Although many aren’t doing in person open houses this year, it may work in your favor that they are digital considering you are a plane ride away. Open houses were a great way to learn about a bunch of schools without the pressure of an in-person interview. I loved that many of them had panels which is something you usually don’t get until accepted student day if you only do personal tours. We learned more useful general information at open houses (especially about their academic support) than we did on tours, so it was useful for us as and we could then craft more specific questions for the schools we were interested in. I also felt it helped DS in interviews to have more knowledge about the school before he had in-person interviews and, just like college recruitment, it shows that you have a true interest in the school rather than just “checking it out” and sticking around for an interview because you flew in.
I would focus on the academic support components of the schools you are looking at. Boarding school is such a wonderful experience but if you are really struggling academically how much of the things that are wonderful about it will you have the bandwidth to truly enjoy? I was hesitant to pick schools that considered “academic support” to be student run tutoring. That might be acceptable for kids that just need a tutor because they missed something in class or it goes a bit fast for them, but not someone with an identified learning disability that needs specific interventions, remediation or accommodations.
As your son has 2 identified LD’s, I’m assuming you’ve had a neuropsych done. I found it helpful to send my son’s neuropsych to the director of academic support at the schools we were interested in to see if he was a good fit for the school. Not only did I get good feedback about the services that they were able to provide, but how they could also accommodate him in the most challenging classes. It gave me a really good feel for if my son would be comfortable with the people he was working with and how the program was integrated into the school. (We is a kid that HATES to be identified in anyway as having an LD).
I know it’s outside of your geographic area, but your son sounds like a perfect fit for New Hampton. I just checked their website and they have a few digital events coming up. It might be a good low stakes way to see if you might want to add them to your list. And if you end up considering heading north, I’d also check out NMH, Suffield and possibly Kimball-Union. Kimball Union seems to have an ongoing series of virtual admission events that look really interesting.