The last MAJOR player that had reason to flip a station was when CBS blew up WBCN, moved formats and calls, and took what was a historically under performing property ( WBCN was 16th in it's final book IIRC) and made a run at the competition ( 850 WEEI, and affiliated stations) in the war of sports stations.
I think we can all agree, that CBS took a gamble and won, not like they had anything to lose if you ask me.
Now the next question, knowing CC owns 94.5 and 107.9, basically owning the youth demographic in the market, is who (assuming major player) has an under performing, under billing station, that would have nothing to lose if they flipped it?
IMHO none of the majors have a station to risk, or the budget to do it.
I'm open to hear others opinions, agreeable or not.