According to elsewhere the for profit had the trademark first, and then handed it over to the nonprofit while remaining a licensee. (Automattic founded 2005, WordPress foundation founded 2010) That's a very above board move. And it makes sense for the for profit to take on the legal aspects, because the extraordinary spend won't ruffle donors feathers.

I'm not sure I understand the reasoning here. Either they are licensee or they're not. The history leading up to that doesn't convey any special rights or exceptions.

And referring to that transfer as "very above board" makes it sound like you're talking about the same thing as the commenter above when in fact you're talking about different things. Because however gracious you find that decision to be, that's a different subject than whether it's above board to, subsequently commingle those responsibilities. And whether or not you feel it's practical, in some sense, it doesn't seem to have anything to do with anything. Either Automatic has The authority to collect licensing payments on behalf of WordPress or they don't and that should be reflected in a charter or something, somewhere.

I don't think referencing the history of Automatic previously owning the trademark has anything to do with anything in this context.

There's pretty broad license for for-profits to share IP with non-profits, e.g. Novartis + GNF, or generally speaking, any university and any spinoff (I refuse to call them startups) created by professors thereof. If you think what automattic is doing seems legally sketchy, you may want to recalibrate your expectation of what sketchy is and just how much the industrial complex of the US would simply not work (for better or worse -- i for one think it would be better, fwiw) if it adhered to your standards.