New York definitely has parallels to Chicago. CBS has three music FMs in NY and all are doing well and none are likely to be flipped any time soon. CBS has three AMs, sports WFAN and two all-newsers, WCBS-AM and WINS. NY is the only market that has two all-news stations and they are both successful. CBS' NY AMs are successful because they are live and local.
WABC, despite being almost all-syndicated except for Joe Crummey, is doing well. Their sister FM, hot AC WPLJ, doesn't do well in NYC, but bills very well because they have high ratings in the LI and NJ suburbs. Cumulus isn't likely to mess with either one of them.
WEPN, like WMVP, is owned by Disney and sold it's only FM, WPLJ, to Citadel, now Cumulus. Speculation has had it for nearly three years that WEPN would migrate to FM at 101.9, currently Emmis' WRXP, a low rated rocker, but Emmis refuses to sell despite being NYs lowest rated full-power FM. For now, WEPN has nowhere to go. WEPN is a directional AM and barely makes a dent against 50 kW blaster WFAN. WEPN has three NY sports teams, the Jets, Knicks and Rangers. Fans of those teams have a hard time dialing in their games. The Yankees are rumored to be talking with WEPN about moving their games there in 2012, but IMHO that could only happen if WEPN gets on FM. The Boston Red Sox actually get more money, $18MM, for their radio broadcasts than do the Yankees, $13MM. The Yankees are currently on 50 kW blaster, WCBS-AM.
I haven't listened to music on FM since subscribing to Sirius in 2003. I only listen to WFAN and WCBS-AM. The only FM I bother with is WKXW (NJ 101.5), NJ's talk and information station. I get my music from satellite and the internet and I'm a geezer as well!