I worked at a firm once that hired a young legal counsel simply because he had recently graduated, and had more knowledge in the recent laws and practices governing internet, digital, mobile, etc. The established counsels were older and less knowledgable, so it's pretty obvious that things HAVE changed since 1999. I'd say they've probably changed since the first JJ movie-- Facebook was still relatively young, Youtube was only a year old, and Kickstarter was still 3 years away from its first million dollar campaign.
If you look at Paramount, their entire executive leadership team is different from what it was when Gerrold was last involved with them (and I don't think any were with the company earlier than 2002). Most were brought in after 2006-- after Enterprise was off the air. Their legal department is fairly new as well, with many who joined the company after 2009.
David Gerrold knows more about Hollywood thinking than you or I perhaps-- but mostly he knows Hollywood from the 80s-- and to say he knows their motives or how they operate or manage Star Trek and decide legal matters is more than a stretch.