Dear Thelittle,
First some small quibbles. 1)Maybe I doubt your second point as well. Maybe too many people think that the average yeshiva guy is a true learner. 2)I do not know why, but some people with excellent middos had to suffer through unhappy marriages until they got divorced. Marriage is a unique relationship, just because they treat each other well, does not mean they can build a happy home together. 3)Getting married without a plan is not the same as getting married because everyone else is. 4) There is a focus today on end of Kollel training. Long Term Kollel is good training for relationships in the workplace. (Except for the other gender part.)
What you wrote about learning and middos can be true up to a point. Once a boy gets to extreme erudition of shas, he must have overcome his personal tendencies. Someone who learns a lot, but is stuck on their own worldview will stall in his Torah knowledge. The Torah demands subservience of our experiences to it’s Eternal Truths. An ignoramus is not bothered by this demand, because he does not learn enough. The Torah gives him what he needs to support (almost) any idea he chooses. He does not know enough to see that Torah also challenges his ideas and remakes them. An average yeshiva boy will stick to topics that fit his experiences, so he is also not challenged to much. And, over time the Torah molds his thinking.
But someone who learns through all of shas and beyond, Is constantly being challenged to mold themselves to the Torah ideal. If they do not follow through on the inner work, they will miss out on the underlying concepts that bring The Whole Torah together. And ‘extreme erudition of shas’ will elude them. I believe this to be the meaning of the story with Rav Chaim Vital and his student. Along with Rav Moshe Feinstein’s Torah comes Rav Moshe Feinstein’s Middos. To be precise, Rav Moshe Feinstein’s extreme Middos brought about his greatness in Torah.