2) To be a better listener, you need to be able to ask specific questions. I, for one, would be highly interested in a list of conversation items to drill this on, since generating these on the spot has been my failure point more times than I can count. (I don't mean trying to prepare follow-ups to everything someone might say, but rather practicing to get better at generating.)

I think you are right on target.

My Dad taught me to ask about peoples' kids, work or hobbies, because people like to tell others about them. I've found it to be a pretty useful tip.