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Trademark law doesn’t stop you from using a word as part of your domain, or referencing other brands as you see fit, as far as I know. Trademark is about protecting a certain brand and making sure people know the source of the product you are representing. Multiple disclaimers throughout the site make it very clear they are not affiliated with Automattic. Having a policy isn’t the same thing as controlling the law. Everyone who runs a wordpress site does or should know the difference between a domain like thewordpresshelpers.com and wordpress.org, especially with the disclaimers spelling it out through the site. I for one wouldn’t want apple to start suing everybody with mac guru in their domain name, or have the right to, since they don’t claim to be affiliated with apple and there is no reasonable cause for confusion.
For example, http://www.the-mac-guru.com and http://www.themacguru.net clearly complement apple, not directly compete with them. I think what Facebook does, try to sue obvious parody or fan sites is an attack on free speech too.

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