Yeah I agree; there are several strategies for the game as a question asker. For me when answering (only a few hundred answers across all Stack Exchange sites,

Yeah I agree; there are several strategies for the game as a question asker. For me when answering (only a few hundred answers across all Stack Exchange sites, so I'm already in the "tail" and probably not representative of the typical answerer), I mainly care about whether the question seems interesting and challenging to me (I'm especially likely to answer if I think no one else would answer). But the point remains that with several thousand questions being asked a day on Stack Overflow, most potential answerers are indeed likely considering "what question is worth the time to answer it" as you said, so a question needs something (effort, interest, broad utility… or just a stroke of good luck) to get "successful". So when asking (~80 questions asked so far across SE sites, only 8 on Stack Overflow), I try to put effort into it (and show it), but ultimately still just treat each question as a gamble and if it doesn't "work out" (question got few/zero/negative votes, or no useful answers) it's no big deal (just lost a turn, try again next time… at least I learned something about what sorts of questions work well on this particular site, and got an opportunity to state my question as clearly as I could, which is often the most useful part of the process). But I can see how people who approach asking questions on StackOverflow from a mindset of "I need help and hope to get it here" can easily get frustrated.