As the no. 1 Obama skeptic on the planet, i’m sorry that my answer is far more succinct and bleak than your own presentation.
Will Obama go All-in with online gambling?
No.
Truth is the guy has never represented fringe issues, going back to when he was a lawyer in Illinois. (And sorry, too, for saying it, as i know it isn’t for us, but this is a fringe issue for the greater populace.) For all his talk, Obama appears already to be as conservative as a Clinton, a Reagan, etc. There won’t be sweeping changes at the federal level to gay rights, marijuana decriminalization, healthcare … or online gaming.
Yes, he can? Well yes, he can feel free to prove me wrong, but i doubt he will.