As long as he was still making money off it, he wouldn't give a damn about Trek. Now if Berman or Braga or Abrams or whoever did something to personally piss him off, then he'd go apeshit, decanonize their work, make them pariahs. But otherwise, he'd be happy to collect money and maybe visit the Trek sets every now and then to chat up the actors.
I don't think that's a problem. I think copyright lasts for something like 75 years after the creator's death. So I think that would count as "getting paid". after 75 years, unless the owners of the copyright do something, it's public domain. So it's still under coryright.