Gene would feel great! He oversaw and was happy with a lot of it over the course of his life.
...what would make him sad is the loss of the integrity. The loss of the message. It's ok if the message of Star Trek is on the side of a cup you paid an outrageous amount for... but if the message was ever lost, that would be damning to the human race as a whole.
Even if Gene needs to convince you to pay for it, or if you can get it for free without merchandise attached, that message of peace, hope, love, and seeking to be a better person at all times in all things, is what is important.
But how would Gene feel about those who were wealthier having an advantage over those who weren't? Is that "humanist" point of view after all then?