Enumerate- Should this item really be on this catagory since it cant be worn and does not have an armor value?
I think you are right. If it cannot be worn, then it is not actually a helmet. It should probably be in the Quest Items category (along with the other pirate-boss' stuff like this).
While we're on the topic, can these items be "equipped"?
I'm guessing not. These should also be moved to Quest Items. I'll add them to the Quest Items page, but I'll wait to update each item page.