The use of WordPress.org shared resources and the WordPress trademarks? I think this isn't all that complicated.
The use of which were already allowed under the existing open source licenses...
In other words, a shakedown by another name.
Also, suggesting that WPE's contributions to the non-profit could be satisfied by paying Matt's for-profit company is almost the textbook definition of private inurement. I don't think he had lawyers familiar with non-profit law clear that offer before he made it. If I worked for the IRS right now WP and Matt would be pretty high on the list of organizations to take a closer look at.
1. The shared resources are baked into Wordpress code, and used by wordpress users no matter which host they are with. Does Matt wish webhosts to fork the repository?
2. Nominative use allows companies to refer to things by their name. It isn't obvious that "Wordpress Hosting" or "Wordpress plugin" is a violation or causes consumer confusion. Does Matt wish for all companies in the ecosystem to stop referring to their products as Wordpress Themes, Wordpress Plugins and Wordpress hosts?
It's worth noting that for years Wordpress.org has routinely referred to companies as "Wordpress hosts"
For example: https://learn.wordpress.org/tutorial/migrating-your-wordpres...
They don't seem to find it confusing and I suspect it would be difficult for Wordpress to launch a legal claim given tolerance of and direct use of those terms.