I think it would be a no brainer for Entercom to come in and extend their WEEI brand into Portland, specifically on WCYI, as they have recently done in Western Mass. Three reasons
1. They're not buying any revenue on the station, so they would be basically paying stick value.
2. No programming costs what so ever.
3. Because it is talk, they can convert the signal to mono and extend the reach even further. No reason to be stereo with sports talk.
The only cost would be to open a sales office in the market. They would also be able to put the Red Sox on it once the contract with the Big Jab expires. JJ would have some issues to deal with, but it would seem like a winner for Entercom.