The corridor of Central Florida that runs through Orlando is famously the most lightning-struck part of the United States, and summer is when it earns the reputation: from June into September, sea breezes off both coasts collide over the middle of the state and detonate into afternoon thunderstorms almost daily. Your chimney is the highest, most exposed thing on the house through all of it. A direct or nearby strike can crack a crown, shatter brick, or shift a stack in ways that look minor from the ground and aren't. After any strike close to the house, the chimney deserves professional eyes.
Even without lightning, the daily storm rhythm is a water problem. Hairline cracks in the crown drink a little every afternoon, tired flashing lets water track along the roofline into the ceiling, and bare masonry absorbs a startling amount over a full storm season. The maddening part is that chimney leaks rarely show up at the chimney: they surface as a stain across the room, peeling paint in a corner, or a damp smell in a spare bedroom. Real chimney leak repair starts with finding the true entry point (crown, flashing, cap, or saturated brick), because sealing the wrong spot just reroutes the water.
Prevention is cheaper than chasing stains. A breathable water repellent applied before the June rains lets brick shed storms instead of soaking them up, and sound flashing closes the joint where most Orlando leaks actually begin. Handled in the drier spring months, chimney waterproofing is a straightforward job; handled after the ceiling stains appear, it comes with drywall work attached.