If you search jailbreak, you find 601 questions at time of writing related to jailbreaking one's device. The legality of this is debatable, but yet these questions are being answered. Should we close questions related to jailbreaking and any other illegal content?
That jailbreak exists should be a tip off to the acceptance of grey-area questions on the site. If they weren't allowed, the tag wouldn't exist, right?
We are not the police and the laws are not uniformly the same from country to country.
So, yes, we do allow some content that skirts in to areas that are legally grey. Jailbreaking being one of them. We'll usually close things that violate the EULA for Apple OSes, but not all questions get closed as some do have merit.