Forgive me, please, for being presumptuous, and for projecting my own feelings and biases on your situation…
What emerges from your posts, write or wrong, is that you’re a particularly intelligent and articulate person. My guess is that you have an advanced secular education, either from schooling or your own efforts (or both). Even your screenname contains a clever pun that bespeaks a love of (not necessarily exclusively Jewish) learning, curiosity and intellectual development.
I would also guess that your son, being your son, has inherited a lot of these traits.
I haven’t read all of your posts, but it’s apparent that you live in a Yeshivish community (you cited your son’s continued wearing of “black and white” as a positive sign of frumkeit.) For better or worse, allowing one’s curiosity about art, science, letters, history, etc. to take hold — the pursuit of knowledge for knowledge’s sake –is not exactly a cherished value in the Yeshivish world, particularly if such learning comes at the expense of limudei kodesh.
There are those who find such an attitude — a repression of one’s natural capabilities and curiosity about the world — to be exceedingly stifling. I have never in my life been Haredi/yeshivish, but in the very brief period of time I spent in a Haredi yeshiva as a 17 year old, I felt that the sense that any activity other than learning was frowned upon and deemed bitul zman was choking me. Because I had been raised in a more modern environment, I knew that this “no-learning-other-than-Torah-learning” attitude was not the only way one could live his Judaism. But I imagine that for what I assume is an intellectually gifted and curious teen like your son, to equate Judaism with a repression of his natural teenage curiosities — to know Yiddishkeit exclusively as a theology that discourages wonderment about anything not found on a blatt Gemara, could very well cause deep resentment of frummkeit, and, ultimately, rejection.
I remember a guy I was friends with in my 20s. Fiercely intelligent. Raised Chasidish. And hated Yiddishkeit because in his view, based on the experiences he had, religious education could only exist to the exclusion of all other kinds of learning. This was a guy who had (and still has) a deep appreciation for music. (By that I mean he doesn’t merely enjoy listening to music…I mean he had a scholar’s appreciation for its intricacies, and an artisan’s talent for working in the medium.) And I think he felt, again, based on his experience, that he could only fully delve into the depths of music if his Judaism was completely left behind.
There are other ways of living a completely orthodox, halachic life. Torah U’Madda may not be a hashkafah that the particularly community you’ve chosen to live in advocates le’chatchilah, but it is a legitimate derech that enables a person to live a halachic life that still allows room for pursuit of one’s natural talents and interests. It is conceivable that your gifted, talented, intelligent son has rejected Yiddishkeit not because of taivos or emunah issues or peer pressure, but simply because in his velt, he doesn’t see societal examples of a way in which he can give full expression to his own, natural, curiosities and interests while still living a fully Torahdik and halachic lifestyle. A person who feels a deep yearning to explore, understand, study and learn may well reject a theology that he feels requires him to stifle those interests. If he were to be exposed to streams of Orthodoxy that don’t require such…well, ‘orthodoxy’….his attitude towards Judaism may well change.
Just my two cents, with a lot of projection, based on my own personal feelings and experiences. I apologize in advance if none of this applies.