So I'm wondering is a simpler question better than a complicated one?
Is an easier understood question considered more helpful?
It's hard to imagine a successful argument to the effect that questions should be more difficult to understand than necessary! So yes, questions should be as easy to understand as you can make them. If you can take a complicated question and make it simple without losing the meaning of the question, then a simple question is certainly better than its more complicated equivalent.
However, simple doesn't necessarily mean "short" or "lacking details." Context is important to help people understand what you're asking; it's only when the reader understands what you're talking about that you can ask a "simple" question. One of the most important functions of comments is to help askers get the amount of context right -- we want them to include some code or details of what they're trying to do, but not too much code or unnecessary details.
Clarity is more important than simplicity. Even if it's never stated explicitly anywhere, clarity is a deeply held value on StackOverflow, and you can see it in the kind of edits we prefer. Edits that remove noise, like "Hi!" and "Thanks," are encouraged. Edits which improve spelling, grammar, or formatting, or which otherwise make a question or answer easier to understand are strongly encouraged. Edits which change the meaning of a post are likely to be rejected unless it's obvious that the goal is to correct an error.