HI and welcome to the EDA forums
OK lets just consider the low power system for a start, 100W
1) 100 W through BNC connectors is probably pushing the limits of the BNC a little bit. You should really be using N type connectors and low loss cable say LDF 4/50 specially with runs of ~ 500ft
2) you need to determine that the transmitter is actually producing its stated 100W ... a quality dummyload wattmeter or one that can have a dunny load attached to its output eg. the trusty Bird 43
3) Then with same meter inline with coax feed and antenna determine the forward and reflected power readings to determine if there may be a fault with either the feed or the antenna.
4) it may entail a further test with the meter on the far end ( antenna end) of the coax with its dummy load to see how much of your 100W is actually getting to the antenna feedpoint
5) inspect the coax visually and carefully looking for any damage
6) inspect the antenna system, checking for corrosion around the feedpoint and anywhere else ... also for physical damage ... brittle failure cracks etc
7) finally if all that checks out OK, you could look at doing some field strength reading around the region it is covering. These could be compared to field strength density maps that you can produce in programs like Radio Mobile
hope that helps some
cheers
Dave