I think Lee's scenario is quite likely, eventually. At one time, buggy whip manufacturing was a good business to be in, too. Creative destruction - paradigm shift - things change. The really odd thing to me is how long this change is taking. I would guess that Government and its associated inertia is what actually is holding back this change. Were radio privatized, terrestrial radio would probably already be dead and buried.
Government tends to protect the moneyed interests. I see nothing wrong with that in moderation. Without the moneyed interests there would be no money invested in anything. For investments to be made, the investor needs to see a good chance for a return on her investment or she won't invest. I believe that Government will continue to do what's best for the moneyed interests. With that in mind I see Dood's central broadcasting facility in every town being licensed to private hands by the FCC, much like the wireless companies are now. The FM band (and the old VHF TV band) has propagational characteristics that favor broadcasting but would be a bad fit for mobile phone usage.
Although I mourn the death of terrestrial radio, it will be interesting to see how all this develops. And of course, I think we old analog radio heads will still be able to plunk away at the shortwave bands throughout our old age and beyond. It's propagational characteristics render it useless for anything but long distance, and worldwide data networks are making that usage obsolete - perfect for we analog dogs!