When the 1996 Telecom Act passed, I think the model was acquire a lot of stations and program them, to a large extent, remotely.
I don't think so. First, the technology and connectivity needed to do that in 1996 was not in place. Satellite distribution was very costly, and only practical with large scale projects with complete simulcasts.
Clear Channel may have been the first to acknowledge that these economies of scale could exist, and they demonstrated that knowledge by advancing the Prophet technology that had been bought by Capstar in 1997 and came to CC via the Capstar / Chancellor set of mergers. It was through design enhancements in the NextGen and, now, the Zetta systems that allowed much of the content sharing to take place.
But it occurred well into the the first decade of the 2000's.
Revenue played along for awhile and costs did drop. While the trend toward digital music was well known in 1996, who could've foreseen the impact the iPod and internet music delivery would have on radio distribution?
Radio distribution does not follow the iTunes / iPad system. It is basically a glorified FTP system that makes resources available at any station across a company, whether those resources are programs, workparts, songs, commercial production or traffic reports.
CC did what it did with WOR to ensure clearance of its top syndicated shows in New York. Cumulus was making threats but ended up keeping Rush in most markets.
Clear had no AMs in New York, and got a big one for a low price. Yes, they could clear a couple of shows but clearance with no listening does not per se create revenue.
I would argue that CC has better leveraged it's product through iHeart. While the whole will likely never be worth what it was acquired for and there will be a restructuring of debt at some point, they have leveraged their many properties and programs into a solid digital product.
But if you look at the revenue, it is still 85% on the AM and FM platforms, not digital. iHeart is a way to transition to new media, but like Pandora, it has no profitable business model until such time as equitable royalty issues for digital distribution are arranged.