Food for thought:
--Both Q and the Loop are being re-engineered for a PPM world. One of the signals will still be a music format, but the other signal would have to be some form of FM talker. Chicago is one of the few markets where AM still generates revenue/ratings, and PPM will only amplify this for the big three (WGN. WLS, WBBM). A Free FM clone is not the answer. But something hipper, faster-paced and targeted for the 30+ listener could move the needle. Oddly enough, the foundation for such a station is in place on The Morning Fix, which can't decide whether it's Daily Show Radio or NPR for Hipsters. If the Fall Out Boy crowd can't embrace it as their morning show, maybe young-end would-be AM newsradio listeners would. The right PD can find the hole it needs to fit and make it work for the format. This also makes sense given their one-PD-for-both-stations strategy.
--Mancow still does not have a flagship station in Chicago. Yes, there's still bad blood there. No, I would not rule out Cow returning to Emmis in some capacity. Yes, his show is much different now, but when his show went away, so did a big a chunk of TSL and revenue. If that sounds too pie-in-the-sky, what other talent does Emmis make a play for (currently in the market or otherwise)? A cume shift has to happen somewhere to make either station a player again, and that can happen sooner than later with the right talent grab.
--Arbitron's white papers on PPM trials in Philly are a few years old, but bear another look:
http://www.arbitron.com/portable_people_meters/papers_presentations.htm Don't think Marv & Co. aren't pouring over ways to exploit PPM's new methodologies. And certainly he, Cummings and Steal have much more recent and compelling data at their disposal on how to do this.
--Clear Channel is not a PPM player and doesn't appear that they will be anytime soon. If CC doesn't encode in Chicago (as is the case in Philly, and subsequently L.A.) what formats/talent can Emmis seize from CC now that gives them leverage when PPM is rolled out?