This doesn't answer all of your thoughts and questions, but when it comes to talking to people without boring them, remember: People love to talk about themselves. Pretend you're a talk show host and just ask things about the other person, about their life, their interests, their work, their hobbies. This is something I learned from the book "How to talk to anyone" by Leil Lowndes. A very helpful read, if you ask me.