Notable that they don't have a single piece of communication from WPEngine indicating that WPEngine at any point entertained the demands as anything Automatic had a legal right to.

Wpengine'a claim was that Matt tried to shake them down last minute before his talk, with specific threats. That appears to be accurate and Matt hasn't disputed it. The term sheet was sent the day before Matt's talk.

What he has provided here is evidence consistent with the idea that Matt had been trying to shakedown WPEngine for a period of a year and a half.

I checked and Wordpress.org refers to sites offering Wordpress hosting services as "Wordpress hosts". Automatic's trademark claim doesn't seem strong in light of industry standards they've allowed and used themselves.