Earlier quoted context omitted.
One issue I run into is finding a Stack Overflow question that exactly matches the issue I've run into, find that it's been closed for being a duplicate, click the link to the question it's supposed to be a duplicate of, and find that the other question is completely unrelated. Not only can I not find the answer from SO at this point, but if I find the answer on my own I can't even help others. Another issue I've run…
The ones that really get my gripe are the ones that are flagged for being off topic.. Off what topic? This is a place where technical questions are asked and answered and this is a technical question that needs answering - Why is it closed?
I think this is a great reflection of one of the largest problems that Stack Overflow has to solve, and that is user education. The definition of what is on topic for Stack Overflow is much more specific than just being "technical", but most users don't even know that.
This results in many new questions being closed. The community is constantly trying to reword these "closed" messages to be as friendly and helpful as possible, but to the newcomer it just feels like rejection.
In many ways, Stack Overflow has solved all it's "technology" problems, and now is left with a lot of psychology and communication problems. The site could definitely use a professional communications specialist.
(FWIW, for those curious, "on topic" is defined here: http://stackoverflow.com/help/on-topic)