One of those two frequencies will be dark forever. The economy, both nationally and in Canton, can't support two operators.
WCER: Ambrozic wants out, Harris (his partner) isn't gonna run the place (hence the LMA to the same guy who ran 1520).
WINW: I call Patrick Barb a mythical owner for a reason. He basically ignored a flurry of FCC deadlines and correspondence. They sent a letter about his renewal problems to his Cuyahoga Falls P.O. Box, which he may not even have anymore (his request for an STA lists his Doylestown home address). The first attempt to resurrect the station was filed at the FCC by the LMA operator's attorney, with a small note from Patrick saying he was OK with it.
Unless two LMA operators who can actually afford to run the things show up, they're probably gone, or sold to an operator who buys them for basically pennies on the dollar...like has happened with some other small AMs in the region.
One of the two survives? Sure. Both? That's a tall order. And the only LMA operator that's run both stations...we have no idea what financial condition he's in, but locked and abandoned studios can't be a good sign.
As far as Ray Jeske goes, my guess is he doesn't feel he needs 900, or more accurately, needs to buy it. I don't know if he intends on permanently replacing that tower or not, and how that works with the FCC, and how much that'd cost him vs. buying a whole new station. (See above about "pennies on the dollar")
But with his regular facility, he still hits Canton, and Massillon is his financial base - he can serve it with either, and he's got a more powerful full time signal in Massillon on 990 than he would with 900.
Interesting idea, but I don't think he bites.