In my Pluralsight course, Using StackOverflow and Other StackExchange Sites, I cover all the things you really need to know to use the sites effectively and get answers to your questions, or a chance to show your skills. In the last module I explain how to help run the sites yourself, and I suppose you don't actually need to know that to use them - but knowing how they're run can help you understand what happens and why, so I included that material. I didn't include things that are really just for fun.
Right now, Winter Bash is on and it's just for fun. I made a quick video to show what it's about - take a look and let me know what you think. I hope to keep adding more "almost-great" items throughout next year.