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The title/hover text for the upvote icon for questions reads "This question shows research effort; it is useful and clear". While clarity is relatively easy to evaluate from the post itself, determining research effort would seem to require at minimum doing a web search unless one knows that the subject is well covered in common sources. Usually I do not bother with a search (and my Google-fu is not reliable) even if I intend to answer the question.

(I was surprised that a search for "fiction avoiding overuse of pronouns" found a few reasonably appropriate pages in the first 20 results, but even the best page, Ask the Editor: How can I cut back on the abundance of pronouns in my writing?, did not seem to provide a thorough answer and took a different tack than my answer, which was more palliative.)

Usefulness seems even more difficult to evaluate. While more specific questions might be less useful typically, some specific questions are obvious cases of a more general problem. Asking about the general problem may be quite useful.

(For answers, usefulness is much easier to evaluate.)

I ask this because many questions seem to receive no upvotes even when the question seems reasonably clear and somewhat useful. Not upvoting such a question and yet answering it seems a bit odd.

Weak questions which might appropriately receive one or two upvotes are especially hard because being the first to upvote a weak question takes some boldness but after being upvoted it is not as clear that the question deserves a second upvote.

"Good subjective" questions are probably more common on Writers than some Stack Exchange sites, but such questions are also more difficult to evaluate.

When should a question be upvoted?

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I completely agree that we need more voting here. But when to do it? Stack Overflow user Jon Skeet put this well in this answer. While he was writing about coding, it's still relevant:

I will upvote a question if:

  • It is clear and well-written, including sample code where appropriate, useful tags etc. Ideally it should indicate that a certain amount of thought has gone into the question too, e.g. "these are approaches I've already tried, but they don't work because of X, Y, Z."
  • It is a non-trivial question which tackles a common source of misunderstanding (e.g. "pass by reference" vs "pass reference by value")

I very rarely downvote questions though - I usually add a comment or vote to close instead.

Your meta post contains a few questions, though:

What is research effort?

I think that "research effort" is a phrasing left over from Stack Overflow, where it was expected that the topic was programming. I think we can assume that the equivalent is the user demonstrating that they've attempted to solve the problem already, and ideally they've told us what didn't work and why.

What is a useful question?

I'd say that it's one that adds to the site, or to the internet in general. Is it a clear problem? Is the question well written? Is it interesting to its intended audience? (Which is writers and editors, on this site.)

Most importantly, is the question written in a way that would interest those with expertise, or is it a question that boils down to "what should I write for this paper/homework assignment/epic cycle of novels/white paper?" (Which we will generally close on-sight.)

You're right that evaluating a subjective question is difficult. But maybe just treat it like any other piece of writing: Is it clear and easy to follow, or do you need to re-read a few times to understand the point?

That's great, but when should I upvote?

The short version: Whenever you feel like it. We're not going to tell anyone how to use their votes. But maybe keep in mind the effect voting has:

Upvoting a question encourages the asker and gives them reputation points. Do you think this question deserves that?

Conversely, is a question horrible enough that it's worth the loss in rep to you to downvote it?

Upvoting makes a question more visible, and attracts more people to it. Downvoting does the opposite.

TL;DR

Upvote stuff you think helps the site, downvote those few questions that you think are harming it. Vote early and often. It'll make the site better.

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  • As the Area 51 page indicates this site "Needs Work" on questions per day and question quality may correlate somewhat. Clarity is somewhat hindered by the subjective nature (yet that subjectivity also makes clarity more important!) and perhaps by less skill in writing, at least in English. (OTOH, programmers are not notorious for clear communication in English, so Stack Overflow must have had similar issues.) I would like to be encouraging, but I also want to rank posts, distinguishing tolerable, decent, interesting, etc. – Paul A. Clayton May 13 '14 at 14:52
  • As I noted, sometimes the usefulness of a question seems to be diminished by specificity. Asking "Is this paragraph spine-tingling?" seems less useful to the site than "How can one make an ordinary setting spine-tingling?" (with the paragraph as an example). On the other hand, a question can easily become too general for SE, requiring an excessively long answer. Critique questions are interesting to site browsers and useful to the asker, but less likely (I suspect) to bring in search traffic (i.e., be useful to non-regulars other than the asker). Anyway, your answer was helpful. – Paul A. Clayton May 13 '14 at 14:53
  • @PaulA.Clayton - Critique questions are a strange beast. They're allowed on the site because having a writers site without a critique function would pretty much make the site useless. I think the hope is that we can find a way to make them instructive too, and hopefully useful to future visitors. – Goodbye Stack Exchange May 13 '14 at 17:50
  • I think answers to critique questions can be useful to future visitors, but finding appropriately helpful answers is probably difficult: not only are search terms generally less obvious than for other sites but even answers addressing a broader issue than the question may not be recognized with the obvious search terms. (E.g., my Nice Answer to 'Alternative word for “she”' never uses "overuse"—but "repetitive"/"repetition" 4 times—though "pronoun" is used 9 times and most of the samples around those presented by a search engine would be helpful. It could still benefit from editing.) – Paul A. Clayton May 13 '14 at 19:07

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