I am not disagreeing with you but I do want to mention that every family, and the relationships within the family, are different. What works with one kid doesn't at all with the other.
For some cadets they appreciate the help with scheduling flights and shuttle rides. I don't think there is a "one-size fits all" approach for this and other topics, such as frequency of phone calls, number of letters or goody boxes.
I don't think it is really about being a "helicopter parent" at this point. Rather it is about renegotiating our relationships with our now adult children and finding ways for them to feel supported and remain a part of their loving families.
Just my thoughts after doing this for a couple of years.
I disagree about writing him every day. Let this young man grow up. He probably is not as needy as his parents. That is not meant to be disrespectful, just my experience.
We want to be reassured all the time. Are they eating right? Are they getting enough sleep? Are the upperclassmen treating him right? We love our kids, but this is the time that they learn to find their own way.
I suggest writing an occasional email. Let him work out his own rides to the airport for visits home. Let him initiate phone calls unless you have something urgent. Let him get his own detergent and buy his own socks. Remember, these kids were picked because they have the right stuff.
A long-time educator, over the years I have seen some helicopter parents that you just wouldn't believe.
You're son is realizing that he is in charge of his own destiny, as it should be.