What I wish I knew…is that, despite our kid badly wanting to head off to boarding school and get away from parents asking about homework, projects, sports, teachers, clubs…there were times when they were homesick, perhaps even a tad scared. It wasn’t obvious to us at the time - kid has close friends and is doing well academically and otherwise.
Somewhat belatedly, we now make a more intentional effort to visit as frequently as possible, or have them come home. Kid is happier, as are we. Wish we had done it sooner.