I want to ask subtle qualitative questions with nuance in the asking and answering. These questions do not always have singular answers, nor do they lend themselves to simple answers. Worse, they frequently have elements of subjectivity, since the nuance needed to answer this class of questions often relies on experiential information and insight.
It's become acknowledged with the professional software developers I've met (in real life) that SO has become fine for elementary "how do I X" (where X is a popular subject and has contributors on SO), but for anything more profound, SO is usually useless (often wrong, even).
Yeah, SO is explicitly designed not to be appropriate for qualitative questions with nuance. The problem is that those kinds of questions can frequently lead to endless debate, there's no clear "right" answer, and so on, and anything where there's voting and marking "accepted" answers and which is designed to be a good resource for someone Googling something to be able to find an answer isn't going to be a good fit for qualitative, subjective, nuanced questions.
I am a professional software developer in real life, and I use SO to ask questions occasionally, and answer questions often. There are definitely plenty of cases where it is much more useful than just elementary "how do I X"; there are lots of cases of real, difficult questions being asked and answered, or lots more of people who are experienced developers but new on a particular language or framework or library asking questions about that. It's also quite good at it's mission, of providing fairly good answers for when you Google a question, rather than a forum post where you have to go to the third page to find a comment that almost, but not quite, actually answers the question, and then two pages further to find the clarification that makes it all actually work.
So, you have to use it for the right kinds of questions, but I find that it really does work fairly well for those. The two main problems are that there is a somewhat low signal to noise ratio, as on any popular forum (lots of beginners asking those basic questions that you mention, lots of people asking questions poorly or unclearly, lots of people jumping on people for not quite asking their question perfectly at first), and that people are a little hasty to close imperfect questions without giving them time to be fleshed out into good questions.
The moderation, voting, and closing of questions is supposed to help with that signal to noise ratio, but I'm a bit skeptical, as it seems to be suppressing a little too much signal, and letting through a little too much noise.
Now, we saw the problems that I described at first (the question was a little bit vague, a lot of people jumped in with hasty and incorrect answers, and it was closed for being too vague), but since the system allows editing, voting, and re-opening of questions, those problems were fixed.
For a lot of questions, if you Google for a question and find it on StackOverflow, there's a very good chance it will be answered correctly. If you find a question that has no answer or was answered incorrectly, you are able to correct it or answer it yourself.
I guess what I'm saying is that StackOverflow isn't perfect, but you really shouldn't write it off based on a single bad experience. Just keep in mind what it is for; questions that are answerable, not just subjective or bikeshed questions, and you need to do at least some effort to ask a good question that has enough detail to be possible to answer.
Just so you know: I have a decently high rep on SO - 21K - and have a highish rep on Programmers.SE. And I spent a fair amount of time on Meta.SO back when unicorns were a good deal more popular. I am not writing this off of a single bad experience: I'm writing this based off about 2 years experience. It's a system - designed at that - that rewards simple questions with simple answers, and is particularly susceptible to wrong answers that are popularly believed. The exception is the nuance and the depth (Clearly, Jon Skeet is part of the exception. :-) ).
I don't particularly care that nuanced qualitative questions can lead to debate. Most things that are interesting and matter can be debated; that's why they are interesting- because there are different perspectives and education and experience can provide the nuance to help with choice. That's why I consider /r/programming a better place to find fruitful discussion than StackOverflow...
Anyway. Hope that helps you in your thought processes.
> Here's an example of StackOverflow working for a fairly deep question, about the maximal possible asymptotic slowdown due to purely functional programming
It's become acknowledged with the professional software developers I've met (in real life) that SO has become fine for elementary "how do I X" (where X is a popular subject and has contributors on SO), but for anything more profound, SO is usually useless (often wrong, even).