Florida is one of the best locations in the USA to put a station. When I traveled around on DX'peditions in Africa and the Pacific, I could always hear stations in Florida when there were
no other stations on the band. Theres also a lot of retired hams down in Florida so you hear them on the air at all sorts of odd hours when the rest of the USA is sleeping.
If Ham A is right on the salt water or in a salt swamp he is going to keep up with the 100 ft tower and probably hear and work DX that nobody else is going hear.
That thing called the brewster angle is what does it if you near saltwater and its worth having. The real problem is that anything near saltwater is expensive in Florida. Then you have all
that noise from all those apartments and the vertical would be the worst antenna to have. If you cant hear them you cant work em!
Then the next problem is that unless the ham is on a small saltwater island his signal will only be good beaming over seawater.
If the Ham in FL is stuck way back from the coast and over poor ground conductivity the vertical is going to be owned by the 100ft tower.
I would take the 100ft tower because you can put together a nice single tower station using either Optibeams, Ultrabeams or Steppirs. For that matter a hexbeam up 100 ft would beat most stations in the city with lower beams
I used to work a station on the Westcoast in Suncity. I think he is a silent key now. He was in a retirement community. He had 3 Butternut vertical that installed as a phased vertical array. He had 60 radials on each antenna.
He had an impressive signal on all bands from 40 through to 10 meters. Where he was the ground conductivity was not very good. His main competition on 40 meters was using the cushcraft 2 element beams. If I blind folded
you and you just listened you could not tell who was using the beam or the butternut phase verticals. His phase verticals worked very well. He used a variable phasing system that was published in one of the ARRL compendium books.
So verticals installed properly can be competitive, just avoid using these no ground all band rubbish verticals.
OK, here is your math problem for today.
Ham "A" is in Key West, Florida, running 1500 Watts to a 1/4 wave vertical with 36 radials of varying lengths.
Ham "B" is down the street from "A", a few hundred yards. He is running barefoot, 200 watts to a Force 12 Tri-bander up around 100 feet.
Assuming both these guys want to work BS7, WHICH One is going to put the most power in the ears of the ISOTROPE on Scarborough?
Obviously, assume all prop, condx, etc. to be equal for the comparison.