I think the "endgame" is to develop their online presence, and IHeartRadio is a step in the right direction, and then begin to dismantle the terrestrial infastructure. It would start by CC selling off the smallest markets to local broadcasters. At this point those markets are almost fully automated anyway, and as long as they get something for them, it will help their bottom line by having less stations to service. In the larger markets, I could see most of their AM properties (with certain exceptions like WLW) being dealt to companies looking to reach minority audiences. Even some rimshot FM's could go in this scenario.
Once all that happens, it would leave the company with a stable of large and major market FM's and a lot less overhead chasing small money in small towns. That portfolio would continue to feed content to their online efforts (as they do now) but the company is smaller, and much more attractive to potential investors in an IPO or takeover bid.