Not bad engineering at all! Especially when it's the owners brother! Honestly, the maximization of this signal is impressive for all its limitations.
If WGSQ would make a simple adjustment to the Nashville side of the signal, Hippie could extend East a bit, but that's asking Zimmer to take his signal out of a lot of population. Population that will never matter, but still.
By my understanding that's not possible. Protection is by station "class"; a station of Class C0 like WGSQ is entitled to 152km of first-adjacent protection from a Class A station like Hippie. WGSQ can reduce power or antenna height, but as long as it remains Class C0, Hippie must remain 152km to its west.
WGSQ could downgrade to C1 by reducing power by 52% (from 100kw to 48kw) or by reducing tower height to 300m or less. (a reduction of 500 feet) That would reduce its protection radius to 133km, allowing Hippie to move 19km to the east. (except that it would run afoul of Fish's 94.1 signal first)
Hippie could move east by using "73.215 short-spacing". However, Hippie still can't increase its signal to the east -- it can move east but must reduce power as it does, to maintain the same signal in the direction of Cookeville. (most stations use directional antennas to accomplish this.) 73.215 gets over my head pretty quickly.