There really might be some good stations, or radio station groups that could be picked up at a bargain for cash, but it would be a very careful choice.
Unfortunately, media properties have been declining in value, and just like house prices, you don't know when the falling will stop. If you can buy it for less cash tomorrow, why buy it today? Still, a lottery winner would have cash, and that is the advantage now when potential buyers are having trouble finding financing. Cash is King.
The things I would avoid are newspapers, which are really in a permanent nose dive, AM stations which also are likely to continue to be declining assets until technology changes, if it does, and even local TV stations have a questionable value future as most viewers get their signals from cable, and satellite and the audience spreads, and with more people getting TV from the internet the value situation for over-the-air TV licenses will just do a faster fade.
So, the bottom line is, probably, take the $300-plus-million and invest it elsewhere, with the possible exception of major FM signals at really bargain prices. Those stations would probably be cheap because an owner must get out, and other potential buyers can't get financing and don't have the cash.