My answer: Leave it open and create a "challenge" tag and flag for such questions.
Obviously the site has general standards for most questions. But even we agree that some questions--notably those in the Purim Torah category--do not need to be governed by such standards.
I think a good way of allowing interesting and fun questions to remain on the site without changing the general standards is making a separate category for semi-out-of-the-box questions.
Since there is a risk that these categories could be abused, the privilege of creating such questions might be restricted to those with significant reputation.
In addition to thinking about what is on the site, we might also consider the question of what is lost to the site by virtue of not falling completely within its current, very strict parameters. I imagine there is a wealth of Jewish questions, mysteries, enigmas and riddles flowing around cyberspace and people's minds. There may come a day when we want to make room for some of it.