[TowerTalk] rooftop tower for satellite array: Central Florida

[normn3ykf at stny.rr.com]

Hi all!
Had a nice conversation with a roofing contractor today. He was quite down on the idea of poking any holes through the roofing material due to the amount of rain at the property (in central florida).
What should I be looking for to properly install ( other than rtfm) and more importantly waterproof the installation so that ingress damage can't happen.
Thanks,
Norm