The Tampa Bay region is famously one of the most lightning-prone places in the country, and Holiday sits right in the pattern: from June into September, most afternoons build toward an hour of violent rain, wind, and strikes. Your chimney is typically the highest and most exposed thing on the house, and it takes that season head-on. Storm after storm, water probes every weakness (a cracked crown, a tired bead of sealant, flashing that lifted a fraction of an inch), and bare masonry simply drinks, absorbing a startling amount of water over a single wet season.
Chimney leaks are sneaky about where they announce themselves. The water gets in at the stack but shows up as a ceiling stain a few feet away, peeling paint in a corner, or a damp smell in a spare room. That is why real chimney leak repair starts with finding the actual entry point rather than caulking the obvious suspect. Sealing the wrong spot does not stop water, it just reroutes it. The junction where chimney meets roof is the most common offender in homes this age, and flashing repair done right ends a leak that roof patches have chased for years.
Prevention is cheaper than drywall. A breathable water repellent, the kind that sheds rain but lets trapped vapor escape, keeps six-decade-old brick from spending every summer saturated. Chimney waterproofing applied ahead of the June rains, on top of a sound crown and cap, closes off the leak paths before the season opens them.