>>47362175Considering that Gen I and II were his love letter to childhood days and kinda commentary on technological advancement tainting these memories, i think that he personally would prefer Pokemon to be over after gen II. He said his story, showed us his views. There's nothing more to add to it.
In some fantastical situation where he would be in charge of one more game i'm pretty sure it would be something darker, grittier and much more murky to show the future where advancement ruined it all. Probably still set in Johto and Kanto but ruined by pollution, wars, criminal activities of Giovanni that would be back from hiatus with new, eviler plan.