Before we get relocated to the Iowa board...
When I was living in this type of enviroment before the days of satellite I used to have a 20 foot mast on the roof with a 6 element FM Yagi and a rotor to get anything decent so I can surely sympathize with your problem.
Looking at the Radio-Locator listing, if I were the owner of either of the two combos in town, I would either quick get a translator for the AM side or run the AM on HD-2 (as several stations are doing in LA - KNX, KABC, retro 1260). Whichever station on AM has the High School Football games would then have a good selling point for HD-2.
HD is not all that expensive. I paid $125 for my car unit (including USB, and MP3 CD) and $55 for my home unit.