The Tampa Bay region has a fair claim to being the lightning capital of the country, and Clearwater sits right in it. From June into September the sea breezes off the Gulf and the bay collide over the peninsula most afternoons and detonate into storms: torrential rain, hard wind, and constant lightning. Your chimney is the tallest, most exposed thing on the house through all of it, taking wind-driven rain from angles that a vertical drizzle never tests.
Chimney leaks rarely show up at the chimney. They show up as a brown ceiling stain a few feet away, bubbling paint near the fireplace, or a damp smell after a storm. Real chimney leak repair starts with finding the true entry point (a hairline crack in the crown, tired flashing where the chimney meets the roof, a rusted cap or chase top, or brick that has simply soaked through), because caulking the wrong spot reroutes water instead of stopping it. On the masonry side, a breathable water repellent applied before the rains lets brick shed storms instead of drinking them; chimney waterproofing ahead of summer is one potentially useful thing a Clearwater homeowner can do for an aging chimney.
Then there is hurricane season, June through November, and on the Gulf side of the peninsula it is not an abstraction: Clearwater residents know exactly how seriously to take a storm in the Gulf. Hurricane-force and even strong tropical-storm winds strip loose caps, peel back flashing, rock unbraced chase tops, and drive rain horizontally into joints. For a chimney fire, suspected carbon monoxide or gas, an unstable chimney, or another immediate danger, leave the area and call 911 or the utility first.