Some important nuance is lost here. Matt Mullenweg transferred the trademark to the WordPress Foundation (which he is head of) and the foundation (again... Matt himself) in turn granted Automattic the exclusive ability to sub-license the name commercially. This is the important bit.
What this means is that any "licensing fee" would be paid to Matt's private, for-profit, VC-backed company (and direct competitor to WPEngine) and there would be zero accountability for how it would be spent.
In practice, the foundation doesn't enjoy any benefit to owning the marks. It's all smoke and mirrors.
The trademark policy sounds like it falls somewhere between the Mozilla Foundation/Corporation model and the Red Hat/Fedora Project model. This is how open source in practice works.
Not really. The Mozilla Corporation and Red Hat aren't direct 1:1 commercial competitors to the people they also license the trademarks to (as is the case with Automattic and WPEngine). It's an obvious conflict of interest and inherently problematic on so many levels.
If there is a real-world open-source analogue to that situation, I'd be genuinely interested in hearing about it.
To me the solution seems simple; The WP Foundation should own and license the trademark. Then use the proceeds for its mission in a way that is accountable to the community (Automattic should not have to pay of course).
What this means is that any "licensing fee" would be paid to Matt's private, for-profit, VC-backed company (and direct competitor to WPEngine) and there would be zero accountability for how it would be spent.
In practice, the foundation doesn't enjoy any benefit to owning the marks. It's all smoke and mirrors.