WOW, It is not up to you to judge how he feels. The truth is you just don’t know, you are just assuming by the way he acts. In truth, you have no way of knowing what he truly feels or what he is truly thinking. He is giving off an aura of “I don’t care, you don’t care, the world doesn’t care, etc.” Therefore the best thing to do is take two deep breathes and thing before speaking. You might just answer “I hear you” which is non judgmental and non-committal. That might not tick him off while giving you the opportunity to acknowledge that you heard him.
It is a good sign that he has “told” you that he is NOT happy with his chevra life. That is NOT a normal thing for a child to do if he doesn’t trust his parents’ love for him. He is tenderly reaching out but still wants to make his own choices. Right now it would seem that he just wants to be heard and not guided. So please just “listen” to understand. Maybe there will be an opportunity down the road in the not too distant future when you will be able to say “In what way can I offer you support with that?” or “how can I support you with that?” Right now he doesn’t seem ready to hear that.