I'd agree, but the repeater hears the subscribers just fine. He's got lots of elevation, but with out knowing the terrain where he is, maybe it's too much gain and the pattern is shooting RF over the coverage area. But with upwards of 500w ERP, you would think that 99sq miles of needed coverage would be saturated and a couple inches of wet noodle would be enough to hear the repeater.
I've never been a fan of side mounted antennas. I've witnessed the effects of tower shielding with sidemounted antennas. I volunteered with a department that had a 4 bay, 1/4 wave spaced dipole array side mounted with out any standoff, and the tower shielding was so bad, a 10 minute drive away, standing with a portable directly behind the antenna, with the tower shielding it, you could hardly hear the repeater.