G..613: I agree with a number of things you wrote. However, the advice you gave is not what the bachur has asked for (even though I agree with your POV). It is one of the reasons why, in your own words, “I see that basically you’ve gotten nowhere.”.
Having a son who deals with bochurim similar to the OP (and I would say on a lower level of ruchniyos than the OP), his approach and advice is different than yours, probably because he understands the “Flatbush” mentality of the bochurim and their parents. Telling the bochur “you have to be willing to leave your comfort zone” does not generally work in these situations. Sometimes we have to adapt to where they are now. bring them up a notch and then do as you suggest.