As for programming not simulcast on all 4 stations - WWCO runs The New York Yankees (and have since before Buckley took over)
Not in 2009 they did.
...and they were doing high school sports. Not sure who tho. Naugatuck Greyhounds (I think their called) are on WATR. WSNG used to carry Torrington Football. Not sure if they still do or not.
Naugy High Greyhounds Football has been a staple on WWCO since 1992. Not sure about '09 as I'm not in the listening area. WATR does more of a game of the week type of thing. Torrington High Red Raider football has been on and off WSNG so I'm not sure what the case is in '09.
Concentrating on one specific high school for football coverage is nothing new to WWCO. I seem to recall WWCO airing Holy Cross High Crusader games in the '80's.