Free lance writer here. I have done a lot of research on copyright issues. The quote a page or two back covers this clearly in my opinion.
Copyright covers a specific picture or story. I can't use that picture or story, or part of a story without the permission of the copyright holder. I can use small portions of it under "fair use" which would allow me to say use a screen print or quote some text in a piece of original writing. Let's say I'm writing an article about the Caleb and Sophia videos. I can reprint a picture of them, or quote parts of the dialog to illustrate a point. Satire is allowed broad discretion to use characters or situations. If they do their own art work and write their own dialog, the Watchtower can't stop the producers of the Simpsons from having fun with Caleb and Sophia.
In the case of the dot org pins, I believe they've trade marked the logo, which is a specific item. But they can't trademark the letters "J" and "W" or ".org" because they are in common use. So anybody can put the letters on anything they want. I've noticed there seems to be a cottage industry advertising such stuff on the internet. From the look of a lot of it, I suspect its small jewelry operations that noticed lots of JW related stuff floating around and jumped on the bandwagon. I don't think they WTBS has any connection to this, and I'm sure they don't have a legal way to stop it. I expect they may get more forceful about telling the sheep not to buy it, unless they set up their own approved source.