I stopped wearing my USNA ring some time ago. I would consider returning it, but I suppose they would just melt it down and reuse it in the “Link in the Chain” program. USNA rings have a small amount of gold from previous graduate rings.
Three of my children went to service academies. I never consciously encouraged them. Today, I would overtly discourage them.
I did that myself. The problem is that the further you progress in rank, the more locked-in you become to the military as a career. That's acceptable when the culture and direction was something with which you agree. But once it shifts into something else, you as a leader are going to be forced not only to accept those policies in silence, but also to parrot and enforce them with respect to your subordinates. And if you speak out or oppose them, you are a disobeying orders.
So right now, a military career as an officer involves either swallowing, parroting, and publicly embracing those ideas, or sacrificing your family's security and getting the boot. Rather than putting yourself into that Hobson's choice, the most rational choice is to avoid military service altogether.
If a kid is good enough to get into an Academy, they'll have plenty of other great career options where disagreement won't mean getting charged under the UCMJ.