FWIW, this is the kind of situation that may best lend itself to an extremely community oriented selling process, basically using the very legitimate position of "saving local Chipley radio."
Consider approaching any-and-all businesses in Chipley and Washington County with one-and-only-one plan that provides them with a 60-second announcement every other hour, 24/7/365, limited to 40-and-only-40 participants for the princely sum of $365 net per month. A dollar a spot. That's 20 spots per hour (4 stop sets with 5 spots each). It amounts to $14,600 a month or $175,200 yearly.
No, you won't get rich. But, yes, if your expectations from this project are appropriately modest, this amount would be enough to keep the thing on the air and--if you focus on gathering & broadcasting local news, local sports, local weather and every damn local event that comes along (yeah, everything)--you could have a nice little local success story on your hands. Involving as many retirees & student interns for fun and/or credit could be a key.
Good luck.