I checked your post history and confirmed the sport. The general answer to your questions is "it depends" on how recruitable he is and what schools he is shooting for.
How good is he? There is a world of difference between top 20 on the junior point list and a C09.
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Are we too early or are we too late?
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Possibly too late. A lot of commitments are made prior to the end of junior year, and there was a lot of recruiting going on at Summer Nationals. I think your Oct. unofficial visit plan is good, but it might have been more productive in the spring of his junior year.
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Do we contact the coaches again if we don't hear from them, and if so, when?
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Yes, I'd call (or, better yet, have DS call) before his college visits to try to set appointments to meet the coaches and see the facilities.
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Do we send a video that we're putting together this weekend at a tournament?
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Only to coaches who express an interest in seeng it.
Congratulations on his success to date and continued good luck to him. It is notable that he has achieved what he has in an environment without much competitive support in the sport. Most coaches will probably recognize that he should progress quickly when given better training opportunities.