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This question has been asked several times in similar (yet often slightly different) ways.

The general consensus seems to be that it's best to ask multiple questions individually in multiple Question posts so that each can be addressed separately. This is as it should be...in general (and in theory!). See related posts for some context and discussion:

In practice, however, it can be more useful to ask a few similar questions if they work together to express a single fundamental concern.

I propose that there are some situations when it is best to ask several questions together, rather than in multiple posts.

For example, sometimes the question-asker finds it difficult to ask something in one question and instead asks it in two or three similar questions to "beat around the bush". This often helps the poster express their fundamental concern more clearly or thoroughly and helps the community understand what the poster is thinking, and why.

Here are a few examples of multiple questions used effectively in a single post:

In these examples, answering one of the questions almost requires answering one of the accompanying questions as well. For this reason, it's better for all if the questioner and answerer each ask and answer these related questions together. Importantly, it also makes the question a much better resource for somebody who stumbles on that that question later, or has a similar question. As pointed out in How to ask multiple similar but different questions?, asking a cluster of questions can help distinguish one question from a near-duplicate and avoid an incorrect flagging as a duplicate.

In other cases (such as How do comments work?), it's probably best to split the questions into multiple posts, but the end result can be a highly-useful repository of knowledge that is a "one-stop-shop".

I'm not satisfied with some SX users demanding separate posts for similar questions if the questions are essentially expressing the same concern. I'm also not satisfied with the prevalence of posts with multiple, disparate questions.

My question is this:

  • When is it okay to post multiple questions?
  • How can we distinguish between multiple questions that ought to be split vs. multiple questions that work together to express a single fundamental concern?
  • What guidelines or standards can we give and enforce for the community?

This is different than the related posts I've seen because I'm looking for guidelines. Whereas this post was asking about how the user should frame his questions in the future, I'm asking what the SX guidelines should be.

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I think that we should always try to ask one question per question on Main sites, irrespective of which of the sites we are using in the Stack Exchange network.

On some sites that is harder to do than on others, but nevertheless I think when multiple questions appear in a question we should do our best to try and get them separated.

As I read questions I am always looking for that single question mark that lets me focus my attention on what precisely the asker is asking.

If there is more than one question mark then I think about whether any of them are really rhetorical and would be better re-written as statements to leave just one.

If there really are multiple questions being asked then I think they should be in separate questions.

My reasons for advocating this are:

  • Some potential answerers may not answer because they feel unable to answer one or more of the questions, so what they could bring to the other question(s) is lost
  • Some answers may correctly address some of the questions but be quite wrong with respect to the others making it hard to decide whether an upvote or downvote is appropriate
  • Askers are likely to be reluctant to accept partial answers, and in the process of waiting for the last question to be answered, end up not accepting any of the answers
  • When there is a single clear question asked, it is so much easier to provide a single clear answer
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