One of the things I've always found extremely ironic about MSE is that the people with the least experience in asking questions and who have perhaps the least perspective on what it's like to ask questions - the ones with the least sympathy - are the ones who we let judge them. High-rep users moderate and close questions; yet a quick check of the first page of highest rep users reveals that they contribute <95% answers (and the only person who even gets close to that is Michael Hardy). Furthermore, it appears that most of them haven't had the experience of a significant number of unsuccessful questions. Medium-rep users are more likely to come back to the site, and so they are the majority of people with the power to vote and comment, essentially determining the success of a question - and again they are more likely to be answerers.
To clarify, the users with high rep often only answer questions, as it appears extremely hard to get rep by asking anything. There are a number of reasons for this:
- A huge number of questions simply go unnoticed, and receive no upvotes. Meanwhile if you answer a question, one is usually very thankful and will upvote even if it's not really good (I've done this tons of time myself). If you are the only answer, you will probably automatically get an additional 15.
- Fortunately the new +10 for an upvote on a question has helped this, but you also get less from asking questions in a literal sense. This is in part due to the acceptance bonus, which I mentioned earlier. There is also the lingering effect of when upvoting an answer was only +5, which IMO was extremely unjust. It takes someone who contributes to the site's knowledge base roughly 5 times as much volume of contribution/time to get to the same rep as someone who has only been answering.
Just from seeing what it's like to review a question, I can see how easy it is to just go with what everyone does and downvote things. It's easy to make up stories about how the person might react when their question is downvoted, that they will find it helpful, realize there's no need to take it personally and that that's just how the site functions, etc. But the truth is that in real world this just isn't how most people - especially low rep users - respond. I can never bring myself to downvote a question, and never have. But it is a feeling that someones who only answers could never understand.