I don't think WOVK is beatable at this point. At least not by the Froggy style, complete with cheese DJ names.
You may pull some shares away from them, but they'd still be #1. You would need to take 9 shares away from them and I can't see that happening.
From a cluster standpoint, going CHR makes the most sense. Kool is tied for 3rd, if you're able to pull Kiss down, you have a #2 station in the market in Kool. By keeping Jack on 96.5, it takes just enough numbers away from Eagle to keep it from going back into double-digits. Retool Jack slightly to focus more on the Classic Rock, and I bet it would perform slightly better. It remains jockless so you're spending no money on it.
You can also then package all 3 FMs. Want to reach the 18-34 and 18-49 audience on WOMP? We'll toss in Jack, they cover 25-54. Want to reach the 35-64 audience on Kool? We'll toss in Jack, and give you 25-54 as well. WOMP could also be sold partly on brand recognition alone. People fondly remember it. Keymarket lacks any strong brand right now. Clear Channel has the 4 biggest in the market in WOVK, Eagle, WK and WWVA.
Knowing Keymarket's love for Froggy though, your scenario wouldn't surprise me.