The dipole is acting as a Near Vertical Incidence Skywave (NVIS) antenna at that height. You should be putting out a decent signal from say 40 to 400 miles from your tx site with it running 100 watts. It could be there aren't a lot of pirate listeners in your area.
Is the dipole flat for it's length? If so there are a couple of quick and dirty tricks to boost the signal from that cloud warmer. The first is to cut a halfwave wire and mount it as counterpoise about a foot off the ground directly below the dipole, don't cut it in the middle, it's not necessary. It will act as a director to enchance the NVIS effect.
You can also cut the halfwave counterpoise, mount it it at the one foot level about a 10th of a wavelength to one side, opposite of where you want the signal to go.
Finally if you want the signal to go both ways re; the dipole, set another counterpoise a 10th of a wavelength to the other side of the low dipole.
Essentially what you're building are NVIS beams. They're cheap as dirt, easy to build and work well in a compromise situation.
Transmitting loops have tendency to cause high voltage fields even at low power. Screwing up TV reception is the least of your worries with them. Hook up that amp to one of the things and you'll be shocking everyone who touches ground or metal within a hundred feet or more of the thing.