I was terrified of big storms when I was a kid. I'll never forget the first time I heard about hurricane damage at Ocean City, MD. I think it was Hurricane Bob--1988? 89? and it washed out the Boardwalk. I didn't want to go on our family beach trip the next year because I was scared that a hurricane would sweep us away. (I was 8-years-old and such a scary-cat little kid. Is is any wonder that I don't ride roller coasters? LOL) Then I found the weather channel and it became my best friend. I would tune in every night during hurricane season and watch for the storms developing.
Hugo was the first storm that I remember watching unfold on TV. We visited Charleston (on our way to WDW) for the first time about 6 months later and I was amazed at the amount of debris that still remained that long after the storm. I'll never forget that the tour guide on our little trolley tour told us that before Hugo, it had been 104 years since the eye on a hurricane had passed through Charleston.
My mom's aunt & uncle lived in Miami half the year when I was a kid and they were home visiting us when hurricane Andrew hit. They sent pictures after they got home. Their neighbor's house was all but destroyed and the only damage at the aunt & uncle's house was debris in the swimming pool and a 100-year-old tree that was uprooted out of their front yard. They have a picture of the two of them standing inside the trunk of the capsized tree.
My parents were on a cruise during Hurricane Jeanne (I think that's the right one). They sailed out of Baltimore to the Caribbean and just missed Jeanne on the way down the coast. While they were there, Jeanne looped around and took another shot at the Florida coast and they just narrowly missed it on the way back as well!
We've only been at WDW for one tropical event--I can't even remember the storm name now (Ivan maybe?). It was August 2012. We were watching the weather closely the week before and I was afraid we were going to have a washout. We had to delay our arrival at EPCOT one day by about an hour. We got caught in a cloudburst at DHS twice, but it was short-lived. Otherwise, it was no big deal and the impact on our trip was minimal.