Congratulations to you DS for a great accomplishment. We face a similar situation, although logistically it is easier to get to Annapolis than New London. We get the same questions about our DD going so far away for school. 90 plus percent of kids here go to the local state university which is in our back yard. We always answer "we are just glad she is in the U.S., for now". We have known since she was 5 or 6 she would go far from home, for school, and life. Your family is in for an amazing ride. Get on board and enjoy.
Please understand this post is to encourage and not discourage. Your family is in for an amazing adventure. Above you have been given much practical advice. I am going to pass along some emotional advice, which is rarely addressed. This can be hard on parents. Your family sounds very much like ours. We are one unit. We do (did) most everything together. When your Mid reports on I-Day, that is it. You don't get to speak to them, outside of 3 20 minute phone calls. Not sure about the rules at USCCA, but I am sure they are every bit as restrictive as USNA. There is a real remorse that ebbs and flows over the summer. It feels like a loss in the family. Karl Smith says it best, "our forth wheel was missing" He does a great job explaining the emotions on his blog mykidlthemid.com. There is a finality to your child being gone, which I can't imagine being the case at a civilian university. You quickly realize on your flight home, your family will never be the same. I am sure all parents come to this realization at some point. Maybe it's that sophomore summer when they decide not to come home from civilian school. I am not sure, but it's a more gradual realization. My DW would get a little bitter at FB post of other Mom's that talked about how sad they were there kid was gone "away" to school 15 minutes across town.
. I had to remind her everyone is going through their processes.
With all that stated, I can't image anything different. Encourage your DS. Enjoy all the pride and good times. The good times are so good. Your DS is obviously exceptional. Would you want him to do what the ordinary kid is doing?