On WCCR's website under the coverage area page, they state that they are currently unable to increase their coverage, but hope to do so in the future. The only thing that they could possibly do would be to sign on a FM translator, assuming that there is an available frequency available that they can work with. Anything that's usable would be limited to very small areas, and would likely require multiple translators to be of any benefit. Not worth the investment for the current ownership.
The other option would be leasing someone's HD sub, which would mostly benefit listeners in WCCR's distant and nighttime coverage areas. Of course, a HD Radio would be required.
As I mentioned before, probably on the old Radio Insight forums, WCCR's broadcast is very problematic southeast of the transmitter. Cities like Kent, Hudson, Cuyahoga Falls, Stow, etc. all fall inside their local daytime coverage contour, yet suffer from weak reception. Possible reasons are either the Cuyahoga Valley weakening the ground coverage of the signal, or the WTAM tower throwing a null in that direction, as it's less than 2 miles from WCCR's transmitter. (Any tower located within 2 miles of a directional AM array must have de-tuners installed to prevent alterations with their pattern).