We've been living in Florida now for three years, and we've yet to encounter tropical weather. The odds of this are apparently wildly unlikely, but here we are. Today we're getting significant rain in advance of a tropical depression that should in earnest cross north of us starting late tomorrow. This won't be a big deal for us (though Tampa is going to get a whole lot of rain), but it's our first taste of tropical stuff.
Diana and I were in Ft. Myers in 2008 for Tropical Storm Fay, which didn't strengthen enough to be a full on hurricane. It was pretty strange to have that consistent strong wind. It was also weird because it didn't really shake the house or anything. We were at my then-future-father-in-law's house, and of course it's concrete block construction. I was surprised at how few people were out and about after it went through.
Being so far inland, Orange County is less at risk than the coasts, where coastal flooding in particular is a big hazard. It's still possible to sustain a fair amount of damage. I recall visiting Orlando in 2004, either between or after one of the three storms that crossed right through Central Florida, and I remember the blue tarps on roofs, visible as the plane landed. That was a crazy anomaly of a year. Fortunately, our house adheres to the latest standards for construction, but you never know.
I imagine the hardest thing in a significant storm would be the power outages. Going a few days without power would be rough.