20:18 Oct 9 

As Nesrin has made clear, the construction "he would not" constitutes a refusal, he did not want to do this thing. It is his "will" not to do this this thing.

19:59 Oct 9 

When this event is at "now" on the time line, the speaker says, "I am telling him not to. But will he listen?" = He will not listen to me telling him not to do this thing". When the event is in the past the speaker says, "I told him not to. But would he listen?" = He would not listen to me when I told him not to do this thing.
This contruction does imply that this behaviour is customary or somehow to be expected, simply because this construction always implies a negative response.

19:34 Oct 9 

Sorry, I haven't had time to dive back into this question until now but I've given some thought to Jim's remarks. He is remarkably well-schooled and is correct that it is the past tense. I believe that he is a bit off about the Yiddish origin. What is very Yiddish is posing a question and then answering it oneself: pure Jewish irony. He does make a truly interesting comment in tracing the "would" to the German "willen". If you keep in mind that "will" as a subject is "voluntad", free will is "libre albedrío" and the adjective "strong-willed" can be translated as "obstinado, terco" and then review Nesrin's very thoughful contribution, you have a good entry point. Both the positive or negative use of the construction is a reference to one person's willingness or unwillingness to do what a second person believes is rational or logical. Usually one builds up a logical argument and then throws in the perception that the other person will not act from the base of that argument, but, rather, as you have suggested, "as is his wont to do". (Sorry that I have used Spanish translations but I don't presume to translate references between English and Portuguese.) I hope

19:02 Oct 9 

So, here WOULD is somewhat of a residue of old WILL as "want to", then, rhetorically, means "didn't/refused - perhaps as is their wont - to do sth?