What if he got landowner permission to put an antenna up in a tree on "Hill B", which is about 700 feet away. If he used RG-11, the losses even at the high end of UHF (700 MHz) would be around 20 dB. A CM-7777 pre-amp has 30 dB of gain, so it seems like this could work? I found a 1000-foot role of RG-11 for only $100. If he put in on "Hill A", the run is closer to 1000 feet but since the signals are about 20 dB stronger there, Hill A might be the better option.
Or maybe even the unmarked hill, (I'll call it Hill C), located about 1000-feet west of Hill B?
Possible coax source:
https://www.cablewholesale.com/products/coaxial-cable/rg11-bulk-...