I feel the same way - I manage okay answering questions but the tough questions I ask typically go unanswered or are never satisfactorily answered. There just isn't incentive for other people to answer them. (The bounty system doesn't work as intended.)
Agreed... If I have a question that I really can't find the answer anywhere else, odds are I'm not going to get a good result on SO either. This is why I've only got 2 questions on my profile. One I eventually answered myself, and one with no helpful answer (but someone did make an effort.)
Most of the questions on SO are easily answered with a proper Google search. It's a skill that should be taught.