Another South Floridian, and weather enthusiast here. Been through many many storms in my lifetime, in Florida and in other places. I guess the worry of a vacation being rained out might be slightly annoying/bothersome, but in general, I don't really find much reason to worry being at Disney during a storm. They're well prepared, have plenty of hard structure shelter spots, and excellent staff and emergency response capability. Personally, rain at Disney never bothered me, but then living here means rain is a strong possibility any day from April through November...and as long as there's not heavy electrical activity, I'll walk around happily in the rain and enjoy the lower crowds.
Last year, we were looking lined up in Irma's crosshair when she was still a Cat 5...that was a bit worrisome...but the last minute weakening and the jog further west before turning kept the Atlantic coast out of the eyewall, so Irma just ended up making a mess but not really damaging much over here. Though spending 4 hours in my pool scooping up hundreds of pounds of leaves and branches that were nearly 3-feet-deep across the pool bottom was NOT particularly fun!:
My house is all hurricane-glass, strengthened roof with small overhang, non-flood zone, and fortified doors and garage, so not much worry riding out most hurricanes here - I might consider evacuating for a strong 5 though.
10 years ago, Hurricane Wilma made much more of a mess in PB County, with the eye and dual eye walls passing directly over our town. No power for 9 days, lots of roof damage throughout the town, and virtually no tree not stripped or felled. 11 years ago, the dual hit of Frances and Jeanne were also messy - 4 days no power after Jeanne, 8 days after Frances...but the loss of power during those two storms was much worse than Wilma because it was still hovering around 93 degrees and humid for both...after Wilma, we had a freak cold front that dropped nighttime temps into the 40s, so being without power wasn't nearly as miserable!
Hurricane Irene, the just miss of Andrew and David, sailing through the gulf right behind hurricane Rita on a cruise ship as we skipped some ports and bailed out for home...and my first hurricane experience way up in New Jersey for Hurricane Bell in the late 70s...I've been close to or in many storms. I've visited islands right after they were crushed by hurricanes, and visited Disney just a few weeks after Charlie tore through.
That's where I get my Disney hurricane experience from - even though I wasn't actually AT Disney during a hurricane. After Charlie tore up Orlando, Hurricane Frances walloped the Atlantic coast of FL, then also passed over Orlando. I needed a break after 8 days in a 100 degree house with no power and all that cleanup, so I booked a last-minute Disney trip, staying at Old Key West with a friend. While there, we got to see all the Charley damage, and the cleanup efforts...and then got the warnings buzzing through Florida that the 4th major hurricane in one year was headed for Florida...Jeanne looked like she was going to hit the same spot Frances did and was headed for Orlando as well. More importantly, my home was just all cleaned up and put back together after Frances and I was no longer there...so I had to make the tough decision to either ride out Jeanne at Disney, then head home and hope nothing happened, or leave Disney early and head home to batten down the house (bring in patio furniture, shut down unnecessary power, fill the tubs, etc). Disney had already begun distributing flyers under the doors telling guests where the shelter spots were, what time to evacuate rooms and head to shelter, and various entertainments planned for kids, food to be passed out, etc. They were prepared! I decided best to head home and make sure all was OK and ready - so I woke the morning that Jeanne was coming ashore and headed south on the Turnpike back towards home. Northbound Turnpike was near-standstill, with bumper-to-bumper traffic for dozens of miles, all evacuating...meanwhile, heading south was...me. Oh, and the occasional emergency truck or police car. Felt kind of stupid being the only car headed INTO the storm while everyone else was trying to get out.
I got home in time to bring in furniture and delicate items, batten down the house, have dinner, and go to bed. Jeanne roared through around 11pm, immediately knocking power back out...the next morning, I woke up, changed for work, drove to a hotel in the next county south, booked a room, threw my suitcase in, and went to work. I wasn't going to spend one single day without power in that heat after going through Frances. A very good decision! A peaceful 4 days in a hotel, then I was able to head back home when power was restored.
Got back up to Disney a month or so later, and in the parks and resorts, there was nary a sign that 3 hurricanes passed overhead. Only when taking the busses between parks and resorts and passing all the forested land did you notice how many trees were felled and stripped of branches.
BTW - I'm headed to Disney Sep 7th for 4 nights. Not worried at all!