For example, say your company ends up on Matt’s legal radar and he trawls the logs looking for accesses from your IPs and says you violated CFAA – even if you’re totally comfortable that you’d prevail in court, that could be an expensive process and discovery might turn up things you’d prefer not to be public. In situations like that it’s easier simply not to risk dealing with him since people who are focused on vengeance will often waste resources on pointless activity just to prove a point.
Somebody should really force the issue to "have standing" to fight the ridiculousness. I'm shocked WP Engine hasn't already
I could see a breach of contract argument too.
IANAL.
For example, if you register on wordpress.org while claiming you have no affiliation with WPE, but you did have any sort of affiliation, they could consider the contract null/void, and claim the access was unauthorised because the contract wasn't valid.
I have a competing product and shouldn't get too far in the weeds on what I truly think here, but the predominant feeling across people that have to interact with this is that it's done on purpose.
It's not so much that people don't understand what the word "affiliation" means, it's that you'd have to be completely certain that a lawyer, hired from what is clearly a litigious org, would have the same understanding.