Sometimes I see a question about a game I'm very familiar with and can indentify strongly with the asker in that the question asked should be answered. Sometimes, their version of the question is horrible, but un-editable without making it 'my' question instead of theirs. In this situation am I screwed because they asked it first, or could I ask somewhat of a duplicate, however, much better question?
I think first and foremost we should try to help the asker ask a better question. Sometimes we know a bit better than they do (otherwise, why are they here?) and education is kind of a key point of the SE network model.
Perhaps a friendly comment along the lines of "Hey, I see what you're trying to do here, but the question may be better phrased as X" or "There's a more fundamental question here you might want to consider" might help. Or "I could use some help understanding your question. Are you trying to ask about Y?" Friendly is always key here.
Sometimes people are going to say "no" when you ask to (potentially radically) change their question. From there, I see two options:
One, if you know the answer to this not-so-great question, and you think you can answer the better question underneath, do that. Sometimes a bad question begs a one sentence answer, but after that sentence we can say "here's some additional info that will help you understand better" and answer the underlying or related issue. This is super win, in my estimation. We helped above and beyond the call.
The second option is to ask a new question. This is more of a last-ditch alternative, in my opinion. By now, we've more or less abandoned this user and the question they're trying to find an answer for, and we've moved on to what's interesting to us "pros." Sometimes we have to do that, and sometimes we really do know better, but it's not a fun experience for the user.
When it comes to duplication, I tend to think that all valid answers on one question should be valid answers to the other, and vice versa. If the questions are different enough that you can't really pass the "answer merge" test, I'm less likely to close as duplicate.