It's appropriate for Drupal to have a trademark policy to protect it from being used to describe products/companies that are not really Drupal.
The trouble is that Dries should not own and protect the trademark as an individual. He has a huge conflict of interest -- the first license he granted for a commercial use was to his own company, Acquia, to create DrupalGardens.com.
The trademark should be owned and enforced by a non-profit, such as the Drupal Association, which will have in its charter the legal requirement that it treat individuals and companies even handedly. Whatever policy the non-profit established for commercial use would be public (Dries does not list his criteria for granting commercial licenses) and benefit the Drupal project as a whole, not an individual.
For six years, before Dries announced he owned the trademark, the name Drupal was freely used by many companies and individuals. This fostered great growth in the project.
If Dries has established a restrictive trademark and license policy from day one, we would not have an open source Drupal movement right now -- the perception that Drupal was not controlled or owned by anyone for their commercial benefit was vital to gaining the participation of tens of thousands of developers.
It is thanks to the work of these tens of thousands of people that the name "Drupal" has value, and a trademark is worth enforcing. That value should be the property of the community, not one person.
I would urge anyone planning on contesting the policy to seek legal representation from an organization such as Electronic Freedom Foundation -- getting your trademark application for a derivative of Drupal denied, and then not having a legal team to fight the decision, only establishes further precedent that the trademark has been properly claimed by Dries.