I dunno. I don't think all of the population demographics are ready for it in the same way that they were for FDR's fireside chats. Back then, many who couldn't afford a radio would go to a relative's home or a neighbor's, or even a department store to hear the President's thoughts and his message for our country. The sense of community was inescapable, and the access was, in many ways, more available even to those uninitiated in the ways of new-fangled technologies.
It is true that senior citizens are the fasted growing demographic on the internet, but they are still the smallest percentage. Besides, when was the last time all of your relatives and next door neighbors came over to watch or listen to anything on your computer? It just doesn't happen, and it doesn't have the same impact. I fear that the days of the fireside chat are over. It was to FDR's credit that he both recognized and capitalized on the phenomenon during the only point in history that it even COULD be effective.
My guess is that if you are looking for another similar window of opportunity, you'll need to wait another 10 to 20 years.