What's daunting is when you don't know the audience-- like opening a new tech support case.
I could write a thorough narrative with a good description of my environment and details of all the things I tried to do. Then I get dismissed by a technician who says (this actually happened): "Your issue is to complicated to be solved over email. We need to have a call." The call lasted less than 5 minutes. It consisted of me reading my email (verbatim, because I'm an asshole and took being dismissed personally), the technician telling me what I needed to do, and me doing it.
I could go with the whole "quick question" route and spend more time than it would take to write having a back-and-forth with a technician who can't let me speak and keeps interrupting with suggestions (for things I've already tried or aren't applicable), repeated questions( because they aren't keeping written notes), or out-right confusion (because they have preconceived ideas about my situation and haven't validated them with questions).
I find it easiest to just grind away on a problem myself, reverse engineering, referring to source code, etc. Then I don't have to feel bad or make someone else feel bad. I loathe having to involve an unknown third-party. My confirmation bias says that it'll usually be bad.